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[ CAS No. 99438-28-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Chemical Structure| 99438-28-5

Chemical Structure| 99438-28-5

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Quality Control of [ 99438-28-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 99438-28-5 ]

SDS Specification

Alternatived Products of [ 99438-28-5 ]

Product Details of [ 99438-28-5 ]

CAS No. :	99438-28-5	MDL No. :	MFCD21332906
Formula :	C₂₁H₃₇BO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	316.33	Pubchem ID :	-
Synonyms :

Safety of [ 99438-28-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 99438-28-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 99438-28-5 ]

[ 99438-28-5 ] Synthesis Path-Downstream 1~55

1
[ 110-62-3 ]
C₁₅H₁₄LiN [ No CAS ]
[ 99438-28-5 ]
[ 148205-06-5 ]
(1R,2R)-1-(diphenylamino)-2-<(1S)-1-hydroxypentyl>cyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide 1) THF, 0 deg C, 2 h, 2) THF, -78 deg C, 3 h, 3) THF, 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

2
[ 124-13-0 ]
C₁₅H₁₄LiN [ No CAS ]
[ 99438-28-5 ]
[ 153898-50-1 ]
(1R,2R)-1-(diphenylamino)-2-<(1S)-1-hydroxyoctyl>cyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide 1) THF, 0 deg C, 2 h, 2) THF, -78 deg C, 3 h, 3) THF, 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

3
[ 555-16-8 ]
C₁₅H₁₄LiN [ No CAS ]
[ 99438-28-5 ]
(1S,2R)-2-Diphenylamino-1-(4-nitro-phenyl)-but-3-en-1-ol [ No CAS ]
(1R,2R)-1-(diphenylamino)-2-<(1R)-1-hydroxy-1-(4-nitrophenyl)methyl>cyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide 1) THF, 0 deg C, 2 h, 2) THF, -78 deg C, 3 h, 3) THF, 12 h, RT; Yield given. Multistep reaction;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

4
[ 100-52-7 ]
C₁₅H₁₄LiN [ No CAS ]
[ 99438-28-5 ]
[ 148205-10-1 ]
(1R,2R)-1-(diphenylamino)-2-<(1R)-1-hydroxy-1-(phenyl)methyl>cyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide 1) THF, 0 deg C, 2 h, 2) THF, -78 deg C, 3 h, 3) THF, 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

5
[ 100-52-7 ]
C₁₅H₁₄⁽²⁾HN [ No CAS ]
[ 99438-28-5 ]
(1R,2R)-1-<(1R)-1-hydroxybenzyl>-2-(diphenylamino)-<3-2H>-cyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

6
[ 75-07-0 ]
C₁₅H₁₄LiN [ No CAS ]
[ 99438-28-5 ]
[ 148205-08-7 ]
(1R,2R)-1-(diphenylamino)-2-<(1S)-1-hydroxyethyl>cyclopentane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide 1) THF, 0 deg C, 2 h, 2) THF, -78 deg C, 3 h, 3) THF, 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

7
C₁₅H₁₄LiN [ No CAS ]
[ 99438-28-5 ]
[ 107-02-8 ]
[ 148205-04-3 ]
(S)-1-((1R,2R)-2-Diphenylamino-cyclopropyl)-prop-2-en-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide 1) THF, 0 deg C, 2 h, 2) THF, -78 deg C, 3 h, 3) THF, 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

8
C₁₅H₁₄LiN [ No CAS ]
[ 99438-28-5 ]
[ 15186-48-8 ]
[ 148261-34-1 ]
(4S)-2,2-dimethyl-4-<(1R)-hydroxy-((1R,2R)-(diphenylamino)cyclopropyl)methyl>-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide 1) THF, 0 deg C, 2 h, 2) THF, -78 deg C, 3 h, 3) THF, 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Barrett; Seefeld [Tetrahedron, 1993, vol. 49, # 36, p. 7857 - 7870]

9
[ 107-05-1 ]
[ 99438-28-5 ]
[ 215728-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium dicyclohexylamide In tetrahydrofuran; diethyl ether; hexane at -95℃; for 1h;

Reference： [1]Hertweck, Christian; Boland, Wilhelm [Journal of Organic Chemistry, 2000, vol. 65, # 8, p. 2458 - 2463]

10
[ 99438-28-5 ]
[ 1730-25-2 ]
[ 106356-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at -78 - 20℃;
	In diethyl ether at -78 - 20℃; for 1.25h;
	In diethyl ether at 0 - 20℃;

	In diethyl ether at 0℃; for 1h;
	In tetrahydrofuran; diethyl ether at 0 - 20℃;
	In diethyl ether for 1h;
	In diethyl ether at 20℃; for 1h;
	In diethyl ether at 25℃; for 1h;
	In diethyl ether at 0℃; for 0.75h;
	In diethyl ether at -78 - 25℃; for 1.5h;
	In diethyl ether at -78 - 20℃; for 1.5h;
	In diethyl ether at 20℃; for 2.5h;
	In tetrahydrofuran; diethyl ether at -78 - 25℃; for 1.25h;
	In diethyl ether at -78 - 20℃; for 1.16667h;
	In diethyl ether at 0 - 25℃; for 1h;
	In diethyl ether at 20℃; for 1h;
	In diethyl ether at 0 - 23℃; for 1h; Inert atmosphere;
	In diethyl ether at 0 - 23℃; Inert atmosphere;
	In diethyl ether at 0 - 20℃; Inert atmosphere;
	In diethyl ether at -78 - 20℃; for 1.25h; Inert atmosphere;
	In diethyl ether at 0℃; for 1h; Inert atmosphere;
	In diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;
	In diethyl ether at -78 - 20℃; for 1.25h;

Reference： [1]Shepherd, Jennifer N.; Myles, David C. [Organic Letters, 2003, vol. 5, # 7, p. 1027 - 1030] Wender, Paul A.; Clarke, Michael O.; Horan, Joshua C. [Organic Letters, 2005, vol. 7, # 10, p. 1995 - 1998]
[2]Bonini, Carlo; Chiummiento, Lucia; Pullez, Maddalena; Solladie, Guy; Colobert, Francoise [Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 5015 - 5022]
[3]Fraunhoffer, Kenneth J.; Bachovchin, Daniel A.; White, M. Christina [Organic Letters, 2005, vol. 7, # 2, p. 223 - 226]
[4]White, James D.; Smits, Helmars [Organic Letters, 2005, vol. 7, # 2, p. 235 - 238]
[5]Castoldi, Damiano; Caggiano, Lorenzo; Bayón, Pau; Costa, Anna M.; Cappella, Paolo; Sharon, Ofer; Gennari, Cesare [Tetrahedron, 2005, vol. 61, # 8, p. 2123 - 2139]
[6]Bolshakov, Sergei; Leighton, James L. [Organic Letters, 2005, vol. 7, # 17, p. 3809 - 3812]
[7]Paterson, Ian; Coster, Mark J.; Chen, David Y.-K.; Gibson, Karl R.; Wallace, Debra J. [Organic and Biomolecular Chemistry, 2005, vol. 3, # 13, p. 2410 - 2419] Crimmins, Michael T.; Haley, Matthew W. [Organic Letters, 2006, vol. 8, # 19, p. 4223 - 4225]
[8]Chen, Zhiyong; Ye, Tao [Synlett, 2005, # 18, p. 2781 - 2785]
[9]Backes, J. Rene; Koert, Ulrich [European Journal of Organic Chemistry, 2006, # 12, p. 2777 - 2785]
[10]Drouet, Keith E.; Theodorakis, Emmanuel A. [Chemistry - A European Journal, 2000, vol. 6, # 11, p. 1987 - 2001]
[11]Pattenden, Gerald; Gonzalez, Miguel A; Little, Paul B; Millan, David S; Plowright, Alleyn T; Tornos, James A; Ye, Tao [Organic and biomolecular chemistry, 2003, vol. 1, # 23, p. 4173 - 4208]
[12]Muir, James C.; Pattenden, Gerald; Ye, Tao [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 20, p. 2243 - 2250]
[13]Nicolaou; Brenzovich, William E.; Bulger, Paul G.; Francis, Tasha M. [Organic and Biomolecular Chemistry, 2006, vol. 4, # 11, p. 2119 - 2157]
[14]Solorio, Dionicio Martinez; Jennings, Michael P. [Journal of Organic Chemistry, 2007, vol. 72, # 17, p. 6621 - 6623]
[15]Chen, Zhiyong; Sinha, Subhash C. [Tetrahedron, 2008, vol. 64, # 8, p. 1603 - 1611]
[16]Hanessian, Stephen; Auzzas, Luciana [Organic Letters, 2008, vol. 10, # 2, p. 261 - 264]
[17]Ghosh, Arun K.; Xu, Xiaoming; Kim, Jae-Hun; Xu, Chun-Xiao [Organic Letters, 2008, vol. 10, # 5, p. 1001 - 1004]
[18]Singh, A. Jonathan; Xu, Chun-Xiao; Xu, Xiaoming; West, Lyndon M.; Wilmes, Anja; Chan, Ariane; Hamel, Ernest; Miller, John H.; Northcote, Peter T.; Ghosh, Arun K. [Journal of Organic Chemistry, 2010, vol. 75, # 1, p. 2 - 10]
[19]Pena-Lopez, Miguel; Montserrat Martinez; Sarandeses, Luis A.; Sestelot, Jose Perez [Organic Letters, 2010, vol. 12, # 4, p. 852 - 854]
[20]Location in patent: experimental part Dubey, Abhishek; Harbindu, Anand; Kumar, Pradeep [Synthesis, 2011, # 6, p. 901 - 904]
[21]Zhu, Kaicheng; Panek, James S. [Organic Letters, 2011, vol. 13, # 17, p. 4652 - 4655]
[22]Sun, Huikai; Roush, William R. [Organic Syntheses, 2011, vol. 88, p. 87 - 101]
[23]Sasaki, Makoto; Iwasaki, Kotaro; Arai, Keisuke [Organic Letters, 2018, vol. 20, # 22, p. 7163 - 7166]

11
[ 18001-18-8 ]
[ 99438-28-5 ]
[ 327628-32-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: allyldimethylphenylsilane With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -45℃; for 2h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 0.5h; Stage #3: With boron trifluoride diethyl etherate at -78℃;
	Stage #1: allyldimethylphenylsilane With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.5h;

Reference： [1]Roush; Pinchuk; Micalizio [Tetrahedron Letters, 2000, vol. 41, # 49, p. 9413 - 9417]
[2]Mertz, Eric; Tinsley, Jennifer M.; Roush, William R. [Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8035 - 8046]

12
[ 590-18-1 ]
[ 99438-28-5 ]
[ 99438-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (Z)-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; for 0.333333h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 0.583333h;
	Stage #1: (Z)-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; for 0.416667h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; diethyl ether; hexane at -78℃; for 0.5h;
	With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane for 1h; cooling;

	Stage #1: (Z)-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - 0℃; for 0.0833333h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.5h; Further stages.;
	Stage #1: (Z)-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; for 0.166667h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
	Stage #1: (Z)-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -42℃; for 0.583333h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; diethyl ether; hexane at -78℃; for 1h; Inert atmosphere; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether; hexane at -78℃; Inert atmosphere;
	Stage #1: (Z)-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; for 0.25h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;

Reference： [1]Zampella, Angela; Bassarello, Carla; Bifulco, Giuseppe; Gomez-Paloma, Luigi; D'Auria, Maria Valeria [European Journal of Organic Chemistry, 2002, # 5, p. 785 - 790]
[2]Colby, Elizabeth A.; O'Brien, Karen C.; Jamison, Timothy F. [Journal of the American Chemical Society, 2004, vol. 126, # 4, p. 998 - 999]
[3]Ramachandran, P. Veeraraghavan; Srivastava, Amit; Hazra, Debasis [Organic Letters, 2007, vol. 9, # 1, p. 157 - 160]
[4]Czuba, Ivona R; Zammit, Steven; Rizzacasa, Mark A [Organic and biomolecular chemistry, 2003, vol. 1, # 12, p. 2044 - 2056]
[5]Nicolaou; Jiang, Xuefeng; Lindsay-Scott, Peter J.; Corbu, Andrei; Yamashiro, Sawako; Bacconi, Andrea; Fowler, Velia M. [Angewandte Chemie - International Edition, 2011, vol. 50, # 5, p. 1139 - 1144]
[6]Wang, Guangwei; Xu, Shiqing; Hu, Qian; Zeng, Fanxing; Negishi, Ei-Ichi [Chemistry - A European Journal, 2013, vol. 19, # 39, p. 12938 - 12942]
[7]Tsuruda, Takeshi; Ebine, Makoto; Umeda, Aya; Oishi, Tohru [Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 859 - 871]

13
[ 624-64-6 ]
[ 99438-28-5 ]
[ 99493-12-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; for 0.333333h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 0.583333h;
	With n-butyllithium; potassium <i>tert</i>-butylate
	With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane for 1h; cooling;

	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; diethyl ether; hexane at -78℃; for 0.5h; Further stages.;
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -45℃; for 0.5h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; Stage #2: (+)-B-methoxydiisocamphenylborane In diethyl ether; hexane at -78℃; for 0.666667h; Further stages.;
	With n-butyllithium; boron trifluoride diethyl etherate; potassium <i>tert</i>-butylate
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; diethyl ether; hexane at -78℃; Inert atmosphere;
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -50℃; for 0.5h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.5h;
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere;
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; for 0.166667h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane Inert atmosphere;	4.5.1.1. (1R,2R)-1-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-2-methylbut-3-en-1-ol 6 To a stirred mixture of potassium tert-butoxide (67 mg, 0.55 mmol, 1.2 equiv, dried at 80 °C/0.5 mm for 8 h) in THF (0.55 mL) and trans-2-butene (0.1 mL, 1.15 mmol, 2.5 equiv) was added n-butyllithium (2.5 M in hexane, 0.22 mL, 0.55 mmol, 1.2 equiv) at -78 °C. The reaction mixture was stirred at -45 °C for 10 min and was subsequently cooled down to -78 °C. (+)-Methoxydiisopinocamphenylborane (1 M in ether, 0.7 mL, 0.70 mmol, 1.5 equiv) was added and the mixture was stirred at -78 °C for 30 min. Boron trifluoride etherate (0.1 mL, 0.80 mmol, 1.7 equiv) was added dropwise. A solution of the aldehyde 5 (200 mg, 0.46 mmol, 1 equiv) in THF (0.46 mL) was then added with a syringe pump (flow rate 5 mL/h) at -78 °C. The mixture was stirred at this temperature for 4 h, treated with 0.40 mL of 3 N NaOH and 0.16 mL of 30% H2O2, and refluxed for 1 h. The aqueous layer was extracted with dichloromethane. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the crude mixture was purified by flash column chromatography (EtOAc/petroleum ether 10:90) to furnish the expected alcohol 6 as a yellow oil (51 mg, 23%).

Reference： [1]Zampella, Angela; Bassarello, Carla; Bifulco, Giuseppe; Gomez-Paloma, Luigi; D'Auria, Maria Valeria [European Journal of Organic Chemistry, 2002, # 5, p. 785 - 790]
[2]Mandal, Amit K.; Schneekloth Jr., John S.; Kuramochi, Kouji; Crews, Craig M. [Organic Letters, 2006, vol. 8, # 3, p. 427 - 430]
[3]Ramachandran, P. Veeraraghavan; Srivastava, Amit; Hazra, Debasis [Organic Letters, 2007, vol. 9, # 1, p. 157 - 160]
[4]Yu; Zhang; Jin [Organic letters, 2001, vol. 3, # 10, p. 1447 - 1450]
[5]Nicolaou; Brenzovich, William E.; Bulger, Paul G.; Francis, Tasha M. [Organic and Biomolecular Chemistry, 2006, vol. 4, # 11, p. 2119 - 2157]
[6]Jung, Won-Hyuk; Guyenne, Sabrina; Riesco-Fagundo, Concepcion; Mancuso, John; Nakamura, Shuichi; Curran, Dennis P. [Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1130 - 1133]
[7]Li, Shuo; Liang, Shuo; Xu, Zhengshuang; Ye, Tao [Synlett, 2008, # 4, p. 569 - 574]
[8]Fang, Lijing; Yang, Jiong; Yang, Fei [Organic Letters, 2010, vol. 12, # 14, p. 3124 - 3127]
[9]Li, Yingfa; Cooksey, John P.; Gao, Zhanghua; Kocieski, Philip J.; McAteer, Stephen M.; Snaddon, Thomas N. [Synthesis, 2011, # 1, p. 104 - 108]
[10]Zhu, Kaicheng; Panek, James S. [Organic Letters, 2011, vol. 13, # 17, p. 4652 - 4655]
[11]Location in patent: experimental part Vuong, Sophie; Brondel, Nicolas; Len, Christophe; Papot, Sébastien; Renoux, Brigitte [Tetrahedron, 2012, vol. 68, # 2, p. 433 - 439]

14
[ 13391-35-0 ]
[ 99438-28-5 ]
[ 474958-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: allyl (4-methoxyphenyl) ether With sec.-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 1h; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.0833333h; Further stages.;

Reference： [1]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Reddy, M. Venkat Ram [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7547 - 7550]

15
[ 99438-28-5 ]
[ 1730-25-2 ]
bis(d-isopinocampheyl)allylborane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at -78 - 20℃; for 1.25h;

Reference： [1]Lafontaine, Jennifer A.; Provencal, David P.; Gardelli, Cristina; Leahy, James W. [Journal of Organic Chemistry, 2003, vol. 68, # 11, p. 4215 - 4234]

16
[ 627-40-7 ]
[ 99438-28-5 ]
<(Z)-γ-methoxyallyl>diisocampheylborane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methylallylether With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.166667h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane at -78℃; for 1h;
	With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h;
	Stage #1: methylallylether With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane at -78℃; for 1h; Inert atmosphere;

Reference： [1]Carter, Kendra D.; Panek, James S. [Organic Letters, 2004, vol. 6, # 1, p. 55 - 57]
[2]Canova, Sophie; Bellosta, Veronique; Bigot, Antony; Mailliet, Patrick; Mignani, Serge; Cossy, Janine [Organic Letters, 2007, vol. 9, # 1, p. 145 - 148]
[3]Location in patent: experimental part Mukherjee, Parag; Sarkar, Tarun K. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 3060 - 3065]

17
[ 99438-28-5 ]
[ 503-60-6 ]
[ 90659-95-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 3,3-dimethyl-allyl chloride With magnesium In diethyl ether at 0 - 5℃; for 1h; Stage #2: (+)-B-methoxydiisocamphenylborane In diethyl ether at 0℃; for 4h;
90%	Stage #1: 3,3-dimethyl-allyl chloride With magnesium In diethyl ether at 0 - 10℃; for 1h; Stage #2: (+)-B-methoxydiisocamphenylborane In diethyl ether at 0℃; for 3h; Further stages.;
90%	With magnesium In diethyl ether (N2); dropwise addn. of alkene to a stirred suspn. of Mg in ether, stirring for 1 h, addn. to a soln. of boron compd. in ether at 0°C, stirring for 4 h; filtration using Kramer's filter, washing with ether, concn. of org. layer, addn. of pentane, stirring for 5 min, sepn. of ppt., evapn., washingwith pentane;

Reference： [1]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Prabhudas, Bodhuri; Pratihar, Debarshi; Reddy, M. Venkat Ram [Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3812 - 3824]
[2]Ramachandran, P. Veeraraghavan; Prabhudas, Bodhuri; Chandra, J. Subash; Reddy, M. Venkat Ram; Brown, Herbert C. [Tetrahedron Letters, 2004, vol. 45, # 5, p. 1011 - 1013]
[3]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Prabhudas, Bodhuri; Pratihar, Debarshi; Reddy, M. Venkat Ram [Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3812 - 3824]

18
[ 75-90-1 ]
[ 77120-79-7 ]
[ 99438-28-5 ]
C₂₉H₄₈BF₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-<(2-methoxyethoxy)methoxy>-2-propene With sec.-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 1h; Stage #3: 2,2,2-Trifluoroacetaldehyde In tetrahydrofuran at -100 - -78℃;

Reference： [1]Ramachandran, P. Veeraraghavan; Padiya, Kamlesh J.; Reddy, M. Venkat Ram; Brown, Herbert C. [Journal of Fluorine Chemistry, 2004, vol. 125, # 4, p. 579 - 583]

19
[ 77120-79-7 ]
[ 99438-28-5 ]
[ 475987-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-<(2-methoxyethoxy)methoxy>-2-propene With sec.-butyllithium In tetrahydrofuran at -78℃; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃;
	Stage #1: 1-<(2-methoxyethoxy)methoxy>-2-propene; (+)-B-methoxydiisocamphenylborane With sec.-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at -100℃; Further stages.;

Reference： [1]Ramachandran, P. Veeraraghavan; Padiya, Kamlesh J.; Reddy, M. Venkat Ram; Brown, Herbert C. [Journal of Fluorine Chemistry, 2004, vol. 125, # 4, p. 579 - 583]
[2]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Reddy, M. Venkat Ram [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7547 - 7550]

20
[ 99438-28-5 ]
[ 78-79-5 ]
[ 128386-22-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isoprene With n-butyllithium; 2,2,5,5-tetramethylpiperidine; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -60℃; for 0.333333h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.0833333h;

Reference： [1]Sparks, Steven M.; Chow, Chun P.; Zhu, Liang; Shea, Kenneth J. [Journal of Organic Chemistry, 2004, vol. 69, # 9, p. 3025 - 3035]

21
[ 624-64-6 ]
[ 99438-28-5 ]
((S)-1-Methyl-allyl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -45℃; for 0.333333h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 1h;

Reference： [1]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Prabhudas, Bodhuri; Pratihar, Debarshi; Reddy, M. Venkat Ram [Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3812 - 3824]

22
[ 77120-79-7 ]
[ 99438-28-5 ]
[1-(2-Methoxy-ethoxymethoxy)-allyl]-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-<(2-methoxyethoxy)methoxy>-2-propene With sec.-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 1h;

Reference： [1]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Prabhudas, Bodhuri; Pratihar, Debarshi; Reddy, M. Venkat Ram [Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3812 - 3824]

23
[ 627-40-7 ]
[ 123-11-5 ]
[ 99438-28-5 ]
[ 913259-99-1 ]
(1R,2R)-2-methoxy-1-(p-methoxyphenyl)but-3-en-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methylallylether With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #3: 4-methoxy-benzaldehyde With boron trifluoride diethyl etherate In tetrahydrofuran; cyclohexane at -78 - 20℃; Title compound not separated from byproducts;

Reference： [1]Kim, In Su; Kim, Ji Duck; Ryu, Chae Baek; Zee, Ok Pyo; Jung, Young Hoon [Tetrahedron, 2006, vol. 62, # 40, p. 9349 - 9358]

24
[ 67-56-1 ]
[ 21947-87-5 ]
[ 99438-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at 0℃; for 2h;
	In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;

Reference： [1]Crimmins, Michael T.; Haley, Matthew W. [Organic Letters, 2006, vol. 8, # 19, p. 4223 - 4225]
[2]Greszler, Stephen N.; Malinowski, Justin T.; Johnson, Jeffrey S. [Organic Letters, 2011, vol. 13, # 12, p. 3206 - 3209]

25
[ 62322-45-6 ]
[ 99438-28-5 ]
[ 132882-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: allyl methoxymethyl ether With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane at -78℃; for 1h;
	With boron trifluoride diethyl etherate; sec.-butyllithium
	With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1.5h;

With CH₃CH₂CH(CH₃)Li In tetrahydrofuran treatment of 1.3 equiv. of allyl ether deriv. with 1 equiv. of s-butyllithium in THF at -78°C for 30 min, addn. of 1 equiv. of 1 M THF soln. of borane deriv. at -78°C, keeping for 1 h; not isolated;

Reference： [1]Yin, Ning; Wang, Guangwei; Qian, Mingxing; Negishi, Eiichi [Angewandte Chemie - International Edition, 2006, vol. 45, # 18, p. 2916 - 2920]
[2]Nicolaou; Guduru, Ramakrishna; Sun, Ya-Ping; Banerji, Biswadip; Chen, David Y.-K. [Angewandte Chemie - International Edition, 2007, vol. 46, # 31, p. 5896 - 5900]
[3]Nicolaou; Sun, Ya-Ping; Guduru, Ramakrishna; Banerji, Biswadip; Chen, David Y.-K. [Journal of the American Chemical Society, 2008, vol. 130, # 11, p. 3633 - 3644]
[4]Nicolaou; Sun, Ya-Ping; Guduru, Ramakrishna; Banerji, Biswadip; Chen, David Y.-K. [Journal of the American Chemical Society, 2008, vol. 130, # 11, p. 3633 - 3644]

26
[ 1826-67-1 ]
[ 99438-28-5 ]
[ 106356-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at -78 - 20℃; for 1h;

Reference： [1]Duffey, Matthew O.; LeTiran, Arnaud; Morken, James P. [Journal of the American Chemical Society, 2003, vol. 125, # 6, p. 1458 - 1459]

27
[ 99438-28-5 ]
C₄₃H₇₅O₃Si₂B [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diethyl ether / 1.17 h / -78 - 20 °C 2: diethyl ether / 2 h / -78 °C

Reference： [1]Solorio, Dionicio Martinez; Jennings, Michael P. [Journal of Organic Chemistry, 2007, vol. 72, # 17, p. 6621 - 6623]

28
[ 7785-26-4 ]
[ 99438-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: BH₃*SMe₂ / tetrahydrofuran / 18 h / 20 °C 2: diethyl ether / 2 h / 0 °C

Reference： [1]Crimmins, Michael T.; Haley, Matthew W. [Organic Letters, 2006, vol. 8, # 19, p. 4223 - 4225]

29
[ 99438-28-5 ]
C₃₄H₅₃BO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sec-BuLi / tetrahydrofuran / 1 h / -78 °C 1.2: BF₃*Et₂O / tetrahydrofuran / -100 °C 2.1: tetrahydrofuran / 2 h / -100 °C

Reference： [1]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Reddy, M. Venkat Ram [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7547 - 7550]

30
[ 99438-28-5 ]
C₃₇H₅₁BO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sec-BuLi / tetrahydrofuran / 0.5 h / -78 °C 1.2: tetrahydrofuran / 1 h / -78 °C 1.3: BF₃*Et₂O / tetrahydrofuran / 0.08 h / -78 °C 2.1: tetrahydrofuran / 2 h / -100 °C

Reference： [1]Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Reddy, M. Venkat Ram [Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7547 - 7550]

31
[ 627-40-7 ]
[ 99438-28-5 ]
C₂₅H₄₄BO₂^(1-)*Li⁽¹⁺⁾=LiC₂₅H₄₄BO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sec.-butyllithium In tetrahydrofuran

Reference： [1]Brown, Herbert C.; Jadhav, Prabhakar K.; Bhat, Krishna S. [Journal of the American Chemical Society, 1988, vol. 110, # 5, p. 1535 - 1538]

32
[ 56-40-6 ]
[ 99438-28-5 ]
(C₁₀H₁₇)2BOCOCH₂NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to glycine in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;
90%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to glycine in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

33
[ 107-97-1 ]
[ 99438-28-5 ]
(C₁₀H₁₇)2BOCOCH₂NHCH₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to N-methylglycine in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, obtaining viscous liquid;
92%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to N-methylglycine in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, obtaining viscous liquid;

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

34
[ 302-72-7 ]
[ 99438-28-5 ]
(C₁₀H₁₇)2BOCOCH(CH₃)NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to alanine in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;
92%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to alanine in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

35
[ 516-06-3 ]
[ 99438-28-5 ]
(C₁₀H₁₇)2BOCOCH(CH(CH₃)2)NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to valine in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;
92%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to valine in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

36
[ 99438-28-5 ]
[ 147-85-3 ]
(C₁₀H₁₇)2BOCO(C₄H₇NH) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to l-proline in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;
90%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to l-proline in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;
66%	In tetrahydrofuran; methanol addn. of soln. of (+)(C10H17)2BOCH3 in THF to l-proline in methanol, stirring at 60-65°C for 0.5 h; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum, washing with ether, recrystn. from methanol/pentane (3:1);

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[3]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

37
[ 150-30-1 ]
[ 99438-28-5 ]
(C₁₀H₁₇)2BOCOCH(CH₂(C₆H₅))NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to phenylalanine in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;
90%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to phenylalanine in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

38
[ 1118-68-9 ]
[ 99438-28-5 ]
(C₁₀H₁₇)2BOCOCH₂N(CH₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to N,N-dimethylglycine in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, obtaining viscous liquid;
95%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to N,N-dimethylglycine in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, obtaining viscous liquid;

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

39
[ 2835-06-5 ]
[ 99438-28-5 ]
(C₁₀H₁₇)2BOCOCH((C₆H₅))NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In tetrahydrofuran; ethanol; water dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to phenylglycine in ethanol/H2O (1:1), stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;
87%	In tetrahydrofuran; dimethyl sulfoxide dropwise addn. of 1 M soln. of (+)(C10H17)2BOCH3 in THF to phenylglycine in DMSO, stirring at 80-100°C; control of completion of the reaction by (11)B-NMR, removing of solvent under vacuum (1-2.0 mm), treating with methanol, filtration, washing with hexane or ether;

Reference： [1]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]
[2]Brown, Herbert C.; Gupta, Ashok K. [Journal of Organometallic Chemistry, 1988, vol. 341, p. 73 - 82]

40
[ 65178-51-0 ]
[ 99438-28-5 ]
B-{(E)-3-(diphenylamino)allyl}diisopinocampheylborane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran metallation of allyldiphenylamine with n-butyllithium in tetramethylethylenediamine at -10°C, transmetallation with (+)-B-methoxydiisopinocampheylborane and BF3*OEt2 at -78°C in THF; not isolated;

Reference： [1]Barrett, Anthony G. M.; Seefeld, Mark A. [Journal of the Chemical Society. Chemical communications, 1993, # 4, p. 339 - 341]

41
[ 19790-60-4 ]
[ 99438-28-5 ]
[ 1730-25-2 ]
(R)-1-benzyloxy-hex-5-en-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.2%	Stage #1: (+)-B-methoxydiisocamphenylborane; allylmagnesium bromide In diethyl ether at -78 - 20℃; for 1.25h; Stage #2: 3-Benzyloxypropanal at -78 - 20℃; for 2h; Stage #3: With sodium hydroxide; dihydrogen peroxide In water for 1h; Heating / reflux;

Reference： [1]Current Patent Assignee: UCKUN - US6335364, 2002, B1 Location in patent: Example 3

42
[ 627-20-3 ]
[ 99438-28-5 ]
[ 887769-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (Z)-pent-2-ene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - -50℃; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; diethyl ether at -78℃;
	Stage #1: (Z)-pent-2-ene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -50℃; for 0.0833333h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere;

Reference： [1]Sonawane, Ravindra P.; Joolakanti, Shyamsunder R.; Arseniyadis, Stellios; Cossy, Janine [Synlett, 2009, # 2, p. 213 - 216]
[2]Greszler, Stephen N.; Malinowski, Justin T.; Johnson, Jeffrey S. [Organic Letters, 2011, vol. 13, # 12, p. 3206 - 3209]

43
[ 646-04-8 ]
[ 99438-28-5 ]
C₂₅H₄₃B [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (E)-pent-2-ene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -78℃; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; diethyl ether at -78℃;

Reference： [1]Sonawane, Ravindra P.; Joolakanti, Shyamsunder R.; Arseniyadis, Stellios; Cossy, Janine [Synlett, 2009, # 2, p. 213 - 216]

44
[ 99438-28-5 ]
[ 1730-25-2 ]
[ 85116-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at 0 - 25℃; for 1h; Inert atmosphere;

Reference： [1]Sinha, Subhash C.; Chen, Zhiyong; Huang, Zheng-Zheng; Nakamaru-Ogiso, Eiko; Pietraszkiewicz, Halina; Edelstein, Matthew; Valeriote, Frederick [Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7045 - 7048]

45
[ 99438-28-5 ]
[ 174155-13-6 ]
[ 1730-25-2 ]
C₅₂H₇₁BO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (+)-B-methoxydiisocamphenylborane; allylmagnesium bromide In diethyl ether at -78 - 20℃; Inert atmosphere; Stage #2: methyl 6-deoxy-2,3,4-tri-O-benzyl-α-D-gluco-hepto-1,7-dialdopyranoside In diethyl ether at -78 - 20℃; Inert atmosphere; stereoselective reaction;

Reference： [1]Ronchi, Paolo; Vignando, Stefano; Guglieri, Sara; Polito, Laura; Lay, Luigi [Organic and Biomolecular Chemistry, 2009, vol. 7, # 12, p. 2635 - 2644]

46
[ 1233347-99-3 ]
[ 99438-28-5 ]
C₃₂H₅₁BOSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: allyl(2-methoxyphenyl)dimethylsilane With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -45℃; for 2.33333h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; Inert atmosphere;

Reference： [1]Dey, Raudra T.; Sarkar, Tarun K. [Journal of Organic Chemistry, 2010, vol. 75, # 13, p. 4521 - 4529]

47
[ 624-64-6 ]
[ 99438-28-5 ]
(+)-B-(E)-crotyldiisopinocampheylborane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - -45℃; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78℃; Inert atmosphere;

Reference： [1]Wang, Lei; Liu, Junyang; Zhang, Hui; Xu, Zhengshuang; Ye, Tao [Synlett, 2010, # 4, p. 563 - 566]

48
[ 7785-26-4 ]
[ 99438-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 20 °C / Inert atmosphere 2: tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

Reference： [1]Greszler, Stephen N.; Malinowski, Justin T.; Johnson, Jeffrey S. [Organic Letters, 2011, vol. 13, # 12, p. 3206 - 3209]

49
[ 624-64-6 ]
[ 99438-28-5 ]
C₂₄H₄₁B [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trans-2-Butene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78 - -50℃; for 0.5h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane for 0.5h; Inert atmosphere;

Reference： [1]Hartmann, Olaf; Kalesse, Markus [Organic Letters, 2012, vol. 14, # 12, p. 3064 - 3067]

50
[ 99438-28-5 ]
C₃₅H₆₅BO₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate; n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - -42 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 1.3: -78 °C / Inert atmosphere 2.1: tetrahydrofuran; hexane; diethyl ether / 3 h / -78 °C / Inert atmosphere

Reference： [1]Wang, Guangwei; Xu, Shiqing; Hu, Qian; Zeng, Fanxing; Negishi, Ei-Ichi [Chemistry - A European Journal, 2013, vol. 19, # 39, p. 12938 - 12942]

51
[ 590-18-1 ]
[ 99438-28-5 ]
((Z)-But-2-enyl)-bis-((1S,2S,3R,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78℃; for 0.5h;

Reference： [1]Feng, Yu; Liu, Jun; Carrasco, Yazmin P.; MacMillan, John B.; De Brabander, Jef K. [Journal of the American Chemical Society, 2016, vol. 138, # 22, p. 7130 - 7142]

52
[ 627-40-7 ]
[ 1076231-00-9 ]
[ 99438-28-5 ]
(2R,3S,4S)-3-hydroxy-4-methoxy-2-methylhex-5-en-1-yl benzoate [ No CAS ]
(2S,3S,4S)-3-hydroxy-4-methoxy-2-methylhex-5-en-1-yl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methylallylether With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane Stage #3: (-)-2-methyl-3-oxopropyl benzoate Overall yield = 75 %; Overall yield = 1.12 g; Further stages;

Reference： [1]Gabba, Adele; Robakiewicz, Stefania; Taciak, Bartłomiej; Ulewicz, Katarzyna; Broggini, Gianluigi; Rastelli, Giulio; Krol, Magadalena; Murphy, Paul V.; Passarella, Daniele [European Journal of Organic Chemistry, 2017, vol. 2017, # 1, p. 60 - 69]

53
[ 107-86-8 ]
[ 99438-28-5 ]
[ 161973-89-3 ]
C₃₄H₆₁BO₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-<<2-(trimethylsilyl)ethoxy>methoxy>-1-propene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #3: 3,3-dimethyl acrylaldehyde In tetrahydrofuran; cyclohexane at -100 - 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Terwilliger, Daniel W.; Trauner, Dirk [Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2748 - 2751]

54
[ 99438-28-5 ]
[ 163041-61-0 ]
C₂₇H₄₉BSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Trimethyl-(2-methylselanylmethyl-allyl)-silane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;	Alcohol 4. To a solution of 6 (1.44g, 6.51 mmol) in THF (15 mL) at -78 °C was added nBuLi (4.4 mL,1.48 M in hexane, 6.5 mmol). After stirring for 5 min, a solution of (+)-Ipc2BOMe (2.05g, 6.48 mmol) in THF (4 mL) was add dropwise, and the stirring was continued for 15 min at the same temperature. To the resulting mixture was added a solution of 8 (0.52g, 2.15 mmol) in THF (3 mL), and the mixturewas stirred for 1.5 h. The reaction mixture was quenched with MeOH, and 3 M NaOH and 30% H2O2 were added at 0 °C. After stirring for 10 min, the resulting mixture was added aq. Na2SO3, and extracted with EtOAc. The organic layer was washed with brine. Concentration and chromatography (CH2Cl2/EtOAc, 50:1) gave 4 (699 mg, 88%)

Reference： [1]Tanaka, Nobuhiro; Takamura, Hiroyoshi; Kadota, Isao [Heterocycles, 2018, vol. 97, # 2, p. 1157 - 1164]

55
[ 99438-28-5 ]
[ 1730-25-2 ]
(+)-B-allyldiisopinocamphenyl borane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at -78 - 20℃; for 1.25h;

Reference： [1]Bharath, Yada; Choudhury, Utkal Mani; Sadhana; Mohapatra, Debendra K. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 41, p. 9169 - 9181]

Same Skeleton Products

Related Products

Historical Records

Similar Product of
[ 99438-28-5 ]

A1003835[ 85134-98-1 ]

Methoxybis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane

Reason: Optical isomers

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere