[ CAS No. 21651-12-7 ] {[proInfo.proName]}

Name: 21651-12-7|(E)-Penta-2,4-dienoic acid|97% mix-50%Z
Brand: Ambeed
SKU: A431965
Rating: 92 (28 reviews)

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Structure of 21651-12-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 21651-12-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 21651-12-7 ]

SDS Specification

Alternatived Products of [ 21651-12-7 ]

Product Details of [ 21651-12-7 ]

CAS No. :	21651-12-7	MDL No. :	MFCD00014017
Formula :	C₅H₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SDVVLIIVFBKBMG-ONEGZZNKSA-N
M.W :	98.10	Pubchem ID :	642034
Synonyms :

Calculated chemistry of [ 21651-12-7 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	26.97
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.62
Log Po/w (XLOGP3) :	1.1
Log Po/w (WLOGP) :	0.81
Log Po/w (MLOGP) :	0.69
Log Po/w (SILICOS-IT) :	0.33
Consensus Log Po/w :	0.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-1.01
Solubility :	9.6 mg/ml ; 0.0979 mol/l
Class :	Very soluble
Log S (Ali) :	-1.48
Solubility :	3.28 mg/ml ; 0.0334 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.29
Solubility :	193.0 mg/ml ; 1.96 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.31

Safety of [ 21651-12-7 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P280-P301+P310-P305+P351+P338-P310	UN#:	2923
Hazard Statements:	H301-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 21651-12-7 ]

* 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.

Upstream synthesis route of [ 21651-12-7 ]
Downstream synthetic route of [ 21651-12-7 ]

[ 21651-12-7 ] Synthesis Path-Upstream 1~4

1
[ 21651-12-7 ]
[ 20069-09-4 ]

Reference： [1] Tetrahedron, 1984, vol. 40, # 1, p. 171 - 176

2
[ 21651-12-7 ]
[ 6052-73-9 ]
[ 61892-77-1 ]

Reference： [1] Tetrahedron, 1984, vol. 40, # 1, p. 171 - 176

3
[ 92892-69-8 ]
[ 29739-67-1 ]
[ 21651-12-7 ]

Reference： [1] Tetrahedron Letters, 1987, vol. 28, # 3, p. 311 - 314

4
[ 21651-12-7 ]
[ 79-10-7 ]
[ 3971-31-1 ]
[ 2305-32-0 ]

Reference： [1] Chemische Berichte, 1953, vol. 86, p. 1312,1317

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Yield	Reaction Conditions	Operation in experiment
72%	With lithium aluminium tetrahydride In diethyl ether Heating;
66%	With lithium aluminium tetrahydride	1 Synthesis of the starting materials. Dimethyl (2-oxohexyl)phosphonate was prepared (33-41% yield) by acylation of dimethyl methylphosphonate with methyl pentanoate using LDA (lithium diisopropylamide) as a base according to a literature procedure (Aboujaoude, E., E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus and Sulfur 1985, 25, 57-61). Pentadienal was prepared from pentadienoic acid according to a literature procedure (Schneider, M. P.; Goldbach, M. J. Am. Chem. Soc. 1980, 102, 6114-6) by LiAlH4-reduction (36-66% yield) and subsequent PCC-oxidation in the presence of sodium acetate (17-46% yield).
54%	Stage #1: (E)-2,4-pentadienoic acid With triethylamine; methyl chloroformate In diethyl ether at 0℃; for 0.5h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #3: With ammonium chloride In methanol

	With lithium aluminium tetrahydride; diethyl ether
	With aluminium hydride
	Multi-step reaction with 2 steps 1: 89 percent / LiAlH₄
	Multi-step reaction with 2 steps 1: 70 percent / H₂SO₄ / 16 h / Ambient temperature 2: LiAlH₄ / diethyl ether / 16 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 64 percent / toluene-p-sulphonic acid / benzene / 50 h / Heating 2: 79 percent / LiAlH₄ / diethyl ether / 3 h / -10 °C
	With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3h; Reflux;

Yield	Reaction Conditions	Operation in experiment
	With trimethylphosphane In dichloromethane
	Ambient temperature;

Yield	Reaction Conditions	Operation in experiment
	With pyridine; oxalyl dichloride In benzene Ambient temperature; 1) 0 deg C, 2) 35 - 40 deg C, 1 h; further reagent: SOCl₂;
	With oxalyl dichloride In benzene for 3h; Ambient temperature;
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere;

[ CAS No. 21651-12-7 ] {[proInfo.proName]}

Quality Control of [ 21651-12-7 ]

Related Doc. of [ 21651-12-7 ]

Product Details of [ 21651-12-7 ]

Calculated chemistry of [ 21651-12-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 21651-12-7 ]

Application In Synthesis of [ 21651-12-7 ]

[ 21651-12-7 ] Synthesis Path-Upstream 1~4

[ 21651-12-7 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In acetone at -10 - 0℃; for 0.5h;
	With N-ethyl-N,N-diisopropylamine In acetone at 0℃; for 0.5h;

Yield	Reaction Conditions	Operation in experiment
70%	In pyridine at 70℃;
57%	In pyridine at 75 - 80℃;
42%	With pyridine for 0.5h; Reflux; Heating;

40%	With pyridine Inert atmosphere;
23%	With pyridine for 1h;
	With pyridine at 100℃; for 4h;
	With pyridine Heating;
	With pyridine at 80℃; for 1h; Inert atmosphere;	3.1.14. (E)-tert-Butyl buta-1,3-dienylcarbamate 19refPreviewPlaceHolder¹⁶ To a solution of malonic acid (5.2 g, 50.3 mmol) in dry pyridine (7.7 mL, 95.6 mmol) heated to 80 °C under an atmosphere of N2 was added 90% acrolein (4.2 mL, ∼51.5 mmol). After 30 min, another aliquot of acrolein (0.3 mL, ∼4.0 mmol) was added. The reaction was heated for a further 30 min then cooled to room temperature. The reaction was quenched by the addition of ice (33 g) followed by cH2SO4 (4.4 mL, 70 mmol) and the mixture extracted with CHCl3 (3×60 mL). The combined organic extracts were dried over MgSO4, concentrated in vacuo to afford (E)-penta-2,4-dienoic acid 18 as a light yellow solid (3.5 g, 72%). The crude material was used immediately in the next reaction without further purification. Crude acid 18 (3.5 g, ∼35.7 mmol) was dissolved in dry Et2O (40 mL) under a N2 atmosphere, the solution cooled to 0 °C and dry TEA (5.5 mL, 39.5 mmol) was added. After 5 min, diphenylphosphoryl azide (8.6 mL, 40.2 mmol) was added and the reaction warmed to room temperature. The reaction was quenched after 1 h with a mixture of satd NaHCO3 (40 mL) and Et2O (40 mL). The organic layer was separated and the aqueous layer extracted with Et2O (3×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The brown oil was passed through a short column of silica (15% EtOAc in n-hexanes to 50% EtOAc in n-hexanes) to afford crude (E)-penta-2,4-dienoyl azide as a bright yellow oil (5.3 g, >100%) that was used immediately without characterization. 3,5-Di-tert-butyl-4-hydroxytoluene (32 mg, 0.15 mmol); tert-butanol (2.8 mL, 37.4 mmol) and dry toluene (40 mL) were heated under reflux. Crude (E)-penta-2,4-dienoyl azide (5.3 g) in dry toluene (15 mL) was added by syringe pump over a 25 min period. The reaction was heated under reflux for 11 h then concentrated in vacuo. The crude oil was purified by flash column chromatography (9:1 n-hexanes/EtOAc) to yield the title compound as a colourless solid (4.1 g, 67% from (E)-penta-2,4-dienoic acid 18).
	With pyridine at 70℃; for 5.5h; Inert atmosphere;
	With pyridine at 80 - 100℃; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; chloroformic acid ethyl ester; diisopropylamine 1.) acetone, 0 deg C, 45 min, 2.) acetone, water, 0 deg C, 45 min; Multistep reaction;
	Multi-step reaction with 2 steps 1: EtN(iPr)2 / acetone / 0.5 h / 0 °C 2: NaN₃ / H₂O / 0.17 h / 0 °C
	Multi-step reaction with 2 steps 1: (i-Pr)2NEt / acetone / 0.5 h / -10 - 0 °C 2: aq. NaN₃ / acetone / 0.25 h / -10 - 0 °C

3.0 g	With diphenylphosphoranyl azide; triethylamine In diethyl ether at 0 - 20℃; for 0.5h;
	With diphenyl phosphoryl azide; triethylamine In diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;	3.1.14. (E)-tert-Butyl buta-1,3-dienylcarbamate 19refPreviewPlaceHolder¹⁶ To a solution of malonic acid (5.2 g, 50.3 mmol) in dry pyridine (7.7 mL, 95.6 mmol) heated to 80 °C under an atmosphere of N2 was added 90% acrolein (4.2 mL, ∼51.5 mmol). After 30 min, another aliquot of acrolein (0.3 mL, ∼4.0 mmol) was added. The reaction was heated for a further 30 min then cooled to room temperature. The reaction was quenched by the addition of ice (33 g) followed by cH2SO4 (4.4 mL, 70 mmol) and the mixture extracted with CHCl3 (3×60 mL). The combined organic extracts were dried over MgSO4, concentrated in vacuo to afford (E)-penta-2,4-dienoic acid 18 as a light yellow solid (3.5 g, 72%). The crude material was used immediately in the next reaction without further purification. Crude acid 18 (3.5 g, ∼35.7 mmol) was dissolved in dry Et2O (40 mL) under a N2 atmosphere, the solution cooled to 0 °C and dry TEA (5.5 mL, 39.5 mmol) was added. After 5 min, diphenylphosphoryl azide (8.6 mL, 40.2 mmol) was added and the reaction warmed to room temperature. The reaction was quenched after 1 h with a mixture of satd NaHCO3 (40 mL) and Et2O (40 mL). The organic layer was separated and the aqueous layer extracted with Et2O (3×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The brown oil was passed through a short column of silica (15% EtOAc in n-hexanes to 50% EtOAc in n-hexanes) to afford crude (E)-penta-2,4-dienoyl azide as a bright yellow oil (5.3 g, >100%) that was used immediately without characterization. 3,5-Di-tert-butyl-4-hydroxytoluene (32 mg, 0.15 mmol); tert-butanol (2.8 mL, 37.4 mmol) and dry toluene (40 mL) were heated under reflux. Crude (E)-penta-2,4-dienoyl azide (5.3 g) in dry toluene (15 mL) was added by syringe pump over a 25 min period. The reaction was heated under reflux for 11 h then concentrated in vacuo. The crude oil was purified by flash column chromatography (9:1 n-hexanes/EtOAc) to yield the title compound as a colourless solid (4.1 g, 67% from (E)-penta-2,4-dienoic acid 18).
	With diphenyl phosphoryl azide; triethylamine In benzene at 0 - 20℃; for 3h; Inert atmosphere;
	Stage #1: (E)-2,4-pentadienoic acid With triethylamine for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With diphenyl phosphoryl azide at 20℃; for 2.5h; Inert atmosphere; Cooling with ice;

Yield	Reaction Conditions	Operation in experiment
90%	In hexane; toluene at 20℃; for 72h;	17 2,4-pentadiene acid 45 (196 mg, 2.0 mmol) and 4-phenyl-l,2,4-triazolin-3,5-dion 46 (350 mg, 2.0 mmol) were dissolved in a mixture of hexane and toluene. The reaction mixture was agitated under inert atmosphere at room temperature for 3 days. After completion of the reaction, the solvent was evaporated, thus giving the Diels-Alder adduct 47 (493 mg, 1.80 mmol, 90 %).
	In ethyl acetate 1.) 0 deg C to r.t., 30 min, 2.) r.t., 18 h; Yield given;
	for 3h; Ambient temperature; Yield given;

Yield	Reaction Conditions	Operation in experiment
13%	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl acetamide at 25℃; for 42h;
13%	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl acetamide at 0 - 25℃; for 42h;	48 EXAMPLE 48 N-[4-(3-Bromo-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl]penta-2,4-dienamide To a 0-5° C. solution of 6-amino-4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidine (160 mg, 0.5 mmol), 80% trans-2,4-pentadienoic acid (245 mg, 2 mmol), and pyridine, (0.5 mL) in 2:1 THF:DMA (3 mL) stirred under N2 was added in one portion 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (490 mg, 2.5 mmol). Cooling was removed, and the viscous mixture was stirred at 25° C. After 23 hours, the mixture was charged with additional trans-2,4-pentadienoic acid (125 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (240 mg), and 2:1 THF:DMA (2 mL). After stirring for another 19 hours, the mixture was diluted with water and ethyl acetate. The biphasic mixture was warmed, then filtered through celite with the filter pad washed well with water and hot ethyl acetate. The filtrate was extracted with ethyl acetate (3*), and the combined organic phases were washed with brine, dried (MgSO4), and concentrated to a solid. The solid was dissolved in hot ethyl acetate and the solution purified by column chromatography over flash SiO2 eluding with ethyl acetate. Product fractions were pooled and concentrated to a solid that was triturated in warm ethyl acetate. After cooling, the solids were collected and dried to leave the product (27 mg, 13%), mp 210-215° C. 1H NMR [(CD3)2SO]: δ 11.04 (s, 1H, exchanges D2O), 10.34 (s, 1H, exchanges D2O), 9.04 (s, 1H), 9.02 (s, 1H), 8.66 (s, 1H), 8.17 (t, J=1.9 Hz, 1H), 7.89 (dt, J=7.7, 1.7 Hz, 1H), 7.40-7.27 (m, 3H), 6.60 (dt, J=16.9, 10.6 Hz, 1H), 6.53 (d, J=15.2 Hz, 1H), 5.75 (d, J=16.9 Hz, 1H), 5.56 (d, J=11.1 Hz, 1H). Mass Spectrum (APCI) m/z (relative %): 395.9 (89), 396.9 (20), 397.9 (100), 398.9 (20). Analysis calculated for C18H14N5OBr.0.3 H2O.0.2 C4H8O2: C, 53.86; H, 3.89; N, 16.70. Found: C, 54.02; H, 3.77; N, 16.33.

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 89 percent / LiAlH₄ 2.1: sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.2: 90 percent / tetrahydrofuran / 18 h / 20 °C
	Multi-step reaction with 3 steps 1: 70 percent / H₂SO₄ / 16 h / Ambient temperature 2: LiAlH₄ / diethyl ether / 16 h / Ambient temperature 3: 70 percent / NaH / tetrahydrofuran / 24 h / Ambient temperature

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 72 percent / chloro-nitroso compound / CH₂Cl₂; ethanol / -10 deg C, 16 h; 0 deg C, 3 h 2: NaHCO₃ / methanol / 5 h / Ambient temperature 3: 55 percent / 5.1M NMO, OsO₄ / acetone; H₂O / 5 h / 40 °C
	Multi-step reaction with 3 steps 1: 75 percent / CH₂Cl₂; ethanol 2: 1.) NaHCO₃; 2.) HCl 3: N-methylmorpholine / OsO₄ / acetone; H₂O / 5 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 75 percent / CH₂Cl₂; ethanol 2: 1.) NaHCO₃; 2.) HCl 3: N-methylmorpholine / OsO₄ / acetone; H₂O / 5 h / 40 °C 4: 2.8 g / Amberlyst-15 / 1.5 h / Ambient temperature 5: Na₂CO₃ / methanol / 1.5 h / Ambient temperature 6: H₂ / 5percent Pd/C / methanol / 2.5 h / Ambient temperature 7: 1.89 g / NaHCO₃ / methanol / 0.25 h 8: 1.) NaBH₄; 2.) aq. 2.5N NaOH; 3.) NaHCO₃ / 1.) i-PrOH, 50 deg C, 6h; 2.) i-PrOH, H₂O, 40 deg C, 6.5 h; 3.) i-PrOH, H₂O, rt, 1 h 9: 1.) Amberlyst-15; 2.) H₂; 3.) HCl / 2.) Pd-C / 1.) EtOH, 80 deg C, 9 h; 2.) EtOH; 3.) MeOH
	Multi-step reaction with 10 steps 1: 75 percent / CH₂Cl₂; ethanol 2: 1.) NaHCO₃; 2.) HCl 3: N-methylmorpholine / OsO₄ / acetone; H₂O / 5 h / 40 °C 4: 2.8 g / Amberlyst-15 / 1.5 h / Ambient temperature 5: Na₂CO₃ / methanol / 1.5 h / Ambient temperature 6: H₂ / 5percent Pd/C / methanol / 2.5 h / Ambient temperature 7: 1.89 g / NaHCO₃ / methanol / 0.25 h 8: NaBH₄ / propan-2-ol / 6 h / 50 °C 9: 1.) aq. 2.5N NaOH; 2.) NaHCO₃ / 1.) i-PrOH, H₂O, 40 deg C, 6.5 h; 2.) i-PrOH, H₂O, rt, 1 h 10: 1.) Amberlyst-15; 2.) H₂; 3.) HCl / 2.) Pd-C / 1.) EtOH, 80 deg C, 9 h; 2.) EtOH; 3.) MeOH
	Multi-step reaction with 9 steps 1: 75 percent / CH₂Cl₂; ethanol 2: 1.) NaHCO₃; 2.) HCl 3: N-methylmorpholine / OsO₄ / acetone; H₂O / 5 h / 40 °C 4: 2.8 g / Amberlyst-15 / 1.5 h / Ambient temperature 5: Na₂CO₃ / methanol / 1.5 h / Ambient temperature 6: H₂ / 5percent Pd/C / methanol / 2.5 h / Ambient temperature 7: 1.89 g / NaHCO₃ / methanol / 0.25 h 8: NaBH₄ / propan-2-ol / 6 h / 50 °C 9: 1.) Amberlyst-15; 2.) H₂; 3.) HCl / 2.) Pd-C / 1.) EtOH, 80 deg C, 9 h; 2.) EtOH; 3.) MeOH

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 75 percent / CH₂Cl₂; ethanol 2: 1.) NaHCO₃; 2.) HCl 3: N-methylmorpholine / OsO₄ / acetone; H₂O / 5 h / 40 °C 4: 2.8 g / Amberlyst-15 / 1.5 h / Ambient temperature 5: Na₂CO₃ / methanol / 1.5 h / Ambient temperature 6: H₂ / 5percent Pd/C / methanol / 2.5 h / Ambient temperature 7: 1.89 g / NaHCO₃ / methanol / 0.25 h 8: 1.) NaBH₄; 2.) aq. 2.5N NaOH; 3.) NaHCO₃ / 1.) i-PrOH, 50 deg C, 6h; 2.) i-PrOH, H₂O, 40 deg C, 6.5 h; 3.) i-PrOH, H₂O, rt, 1 h
	Multi-step reaction with 9 steps 1: 75 percent / CH₂Cl₂; ethanol 2: 1.) NaHCO₃; 2.) HCl 3: N-methylmorpholine / OsO₄ / acetone; H₂O / 5 h / 40 °C 4: 2.8 g / Amberlyst-15 / 1.5 h / Ambient temperature 5: Na₂CO₃ / methanol / 1.5 h / Ambient temperature 6: H₂ / 5percent Pd/C / methanol / 2.5 h / Ambient temperature 7: 1.89 g / NaHCO₃ / methanol / 0.25 h 8: NaBH₄ / propan-2-ol / 6 h / 50 °C 9: 1.) aq. 2.5N NaOH; 2.) NaHCO₃ / 1.) i-PrOH, H₂O, 40 deg C, 6.5 h; 2.) i-PrOH, H₂O, rt, 1 h
	Multi-step reaction with 8 steps 1: 75 percent / CH₂Cl₂; ethanol 2: 1.) NaHCO₃; 2.) HCl 3: N-methylmorpholine / OsO₄ / acetone; H₂O / 5 h / 40 °C 4: 2.8 g / Amberlyst-15 / 1.5 h / Ambient temperature 5: Na₂CO₃ / methanol / 1.5 h / Ambient temperature 6: H₂ / 5percent Pd/C / methanol / 2.5 h / Ambient temperature 7: 1.89 g / NaHCO₃ / methanol / 0.25 h 8: NaBH₄ / propan-2-ol / 6 h / 50 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 72 percent / LiAlH₄ / diethyl ether / Heating 2: 70 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1.5 h 3: 1.) sodium bis(trimethylsilyl)amide / 1.) n-hexane, reflux, 3 h, 2.) THF, -78 deg C, 1.5 h; warm to ambient temperature 4: 55 percent Turnov_. / 72 h / 4 °C 5: pentane / 6 h / 15 °C / Irradiation
	Multi-step reaction with 6 steps 1: 72 percent / LiAlH₄ / diethyl ether / Heating 2: 70 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1.5 h 3: 1.) sodium bis(trimethylsilyl)amide / 1.) n-hexane, reflux, 3 h, 2.) THF, -78 deg C, 1.5 h; warm to ambient temperature 4: 55 percent Turnov_. / 72 h / 4 °C 5: pentane / 6 h / 15 °C / Irradiation 6: hexane / 125 °C / rearrangement
	Multi-step reaction with 6 steps 1: 72 percent / LiAlH₄ / diethyl ether / Heating 2: 70 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1.5 h 3: 1.) sodium bis(trimethylsilyl)amide / 1.) n-hexane, reflux, 3 h, 2.) THF, -78 deg C, 1.5 h; warm to ambient temperature 4: 55 percent Turnov_. / 72 h / 4 °C 5: CDCl₃; CD₂Cl₂ / 0.5 h / -40 °C / Irradiation 6: hexane / 125 °C / rearrangement

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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