[ CAS No. 111-45-5 ]

Name: 111-45-5|2-(Allyloxy)ethanol|95%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 111-45-5 ]

CAS No. :	111-45-5	MDL No. :	MFCD00020607
Formula :	C₅H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GCYHRYNSUGLLMA-UHFFFAOYSA-N
M.W :	102.13	Pubchem ID :	8116
Synonyms :

Safety of [ 111-45-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338	UN#:	1760
Hazard Statements:	H315-H318	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 111-45-5 ]

* 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.

Upstream synthesis route of [ 111-45-5 ]
Downstream synthetic route of [ 111-45-5 ]

[ 111-45-5 ] Synthesis Path-Upstream 1~10

1
[ 107-21-1 ]
[ 106-95-6 ]
[ 111-45-5 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1995, # 5, p. 1022 - 1037
[2] Journal of Organic Chemistry, 1994, vol. 59, # 6, p. 1428 - 1443
[3] Russian Chemical Bulletin, 2004, vol. 53, # 1, p. 137 - 143
[4] Journal of Organometallic Chemistry, 1992, vol. 436, # 1, p. 43 - 53
[5] Biomacromolecules, 2018, vol. 19, # 6, p. 2089 - 2097
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2678 - 2702
[7] Canadian Journal of Chemistry, 1971, vol. 49, p. 2563 - 2577
[8] Bulletin de la Societe Chimique de France, 1970, p. 3070 - 3075
[9] Chemistry of Heterocyclic Compounds, 2003, vol. 39, # 9, p. 1218 - 1226
[10] Synthesis, 2004, # 7, p. 1007 - 1010

2
[ 3973-18-0 ]
[ 111-45-5 ]

Reference： [1] Russian Journal of General Chemistry, 2013, vol. 83, # 1, p. 143 - 145[2] Zh. Obshch. Khim., 2013, vol. 83, # 1, p. 151 - 153

3
[ 107-21-1 ]
[ 107-05-1 ]
[ 111-45-5 ]

Reference： [1] Pharmaceutical Chemistry Journal, 1994, vol. 28, # 2, p. 110 - 113[2] Khimiko-Farmatsevticheskii Zhurnal, 1994, vol. 28, # 2, p. 26 - 28
[3] Journal of Materials Chemistry, 1996, vol. 6, # 1, p. 15 - 22

4
[ 109126-88-7 ]
[ 901-44-0 ]
[ 111-45-5 ]

Reference： [1] Patent: WO2002/6206, 2002, A2, . Location in patent: Page 57-59

5
[ 15022-08-9 ]
[ 107-21-1 ]
[ 96-49-1 ]
[ 111-45-5 ]

Reference： [1] Chemistry - A European Journal, 2012, vol. 18, # 9, p. 2660 - 2665

6
[ 821-09-0 ]
[ 111-45-5 ]

Reference： [1] Tetrahedron, 1979, vol. 35, p. 1365 - 1372

7
[ 75-21-8 ]
[ 107-18-6 ]
[ 111-45-5 ]

Reference： [1] Khimicheskaya Promyshlennost (St. Petersburg, Russian Federation), 1953, p. 104[2] Chem.Abstr., 1956, p. 6384
[3] Journal of Organic Chemistry, 1960, vol. 25, p. 1228 - 1229

8
[ 3984-22-3 ]
[ 111-45-5 ]

Reference： [1] Canadian Journal of Chemistry, 1971, vol. 49, p. 2563 - 2577

9
[ 107-18-6 ]
[ 107-07-3 ]
[ 111-45-5 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1964, vol. 34, p. 2193 - 2197[2] Zhurnal Obshchei Khimii, 1964, vol. 34, # 7, p. 2182 - 2186

10
[ 107-21-1 ]
[ 111-45-5 ]

Reference： [1] Monatshefte fuer Chemie, 1959, vol. 90, p. 787,788,790

[ 111-45-5 ] Synthesis Path-Downstream 1~11

1
[ 5631-96-9 ]
[ 111-45-5 ]
[ 727986-30-3 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 5133 - 5135

2
[ 111-45-5 ]
[ 1000-05-1 ]
C₁₈H₄₆O₇Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-dibutyl amino-2 ethanol In ethanol at 68 - 154℃; for 3h;	20 (RH VIII) a laboratory prepared material obtained from the hydrosilylation reaction between the equilibrate MHD2MH and a 30% molar excess of the 2-allyloxyethanol which has the formula CH2CH-CH2-O-CH2-CH2OH. A nitrogen blanketed glass reactor at atmospheric pressure, which was equipped with a temperature probe, an agitator, a condenser and a nitrogen inlet, was charged with 24 gms of polysiloxane hydride of the formula equilibrate MHD2MH containing 158.8 cc/g of active hydrogen, 22.7 gms of the allyl ether with an allyl content of 40 weight percent; then 54 microliters of dibutylethanolamine was added as a buffer. The reaction mixture (heterogeneous) was heated to 73° C. and platinum catalyst was introduced as 47 microliters of a 3.3% solution of chloroplatinic acid in ethanol, corresponding to 10 ppm of platinum. The reaction was exothermic and the reactor temperature rose to 154° C. after 1.5 min but after 30 min total time the reaction was not complete and an addition of 2g of 2-allyloxyethanol was done at 68° C. to complete the hydrosilation reaction. It will be understood herein that the terms hydrosilation and hydrosilylation are interchangeable. The reaction was complete (i.e., the equilibrate SiH was consumed) after 3 hours. The copolymer was allowed to cool in the reactor for 30 minutes and then removed. The equilibrate MHD2MH was obtained as quoted in example 05.

Reference： [1]Current Patent Assignee: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC. - US2007/249502, 2007, A1 Location in patent: Page/Page column 19-20

3
[ 111-45-5 ]
[ 1189-93-1 ]
C₁₆H₄₀O₆Si₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With platinum⁽⁰⁾-2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane at 70 - 150℃; for 1.33333h;	54 (WARO 2598) is a laboratory prepared material obtained from the hydrosilylation reaction between MHDMH and an allyl started polyether with the formula of CH2CH-CH2-O-(CH2-CH2O)H with the allyl started polyether added in molar excess (30%) in the presence of the Karstedt PTS type catalyst. In a bottle with a magnetic stirrer, a dropping funnel and a refluxing condenser, flushed with nitrogen, 26.26 g of the allyl ether were mixed with 0.1 gram PTS (containing 1% Platinum) and the mixture was heated to 70° C. Then 13.4 g of MHDMH was added dropwise during 20 minutes. The system heated up by itself up to 150° C. during the hydrosilylation. The mixture was further stirred for 60 min at 140° C. and left for cooling down. The reaction product was predominantly Si-C linked as seen by NMR. The weight of the product obtained was 45.5 g. The equilibrate MHDMH was obtained as follows: 600 g of MHDMH were obtained from the equilibration of 1025g MHMH and 3800g of MHD2MH (see preparation in example 05) in the presence of 120 g Levatit K2641 (a sulphonic acid modified polystyrene ion exchanger available from Lanxess) under reflux for 3 hours (the temperature went up to 97° C.), and after cooling, the ion exchanger Levatit was filtrated through a folded paper filter with a pore size of 10 μm. The final product was distilled to get a product with 96% purity.

Reference： [1]Current Patent Assignee: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC. - US2007/249502, 2007, A1 Location in patent: Page/Page column 25

4
[ 111-45-5 ]
[ 2370-88-9 ]
C₂₄H₅₆O₁₂Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In toluene at 100℃; for 12h;	1 In 100 mL of toluene was dissolved 2,4,6,8-tetramethylcyclotetrasiloxane(D4H) (10 g, 0.0426 mol). Then, Pt(O) catalyst was added and the allyloxyethanol(AOE, 18.68 g, 0.17 mol) dissolved in 150 mL of toluene was added dropwise. After12 hours of reflux at 100 0C under nitrogen atmosphere, the mixture was cooled toroom temperature and stirring was performed after adding activated carbon.About 24 g of D4-2,4,6,8-tetra(ethoxyethanol) (D4OE, n = 1) was obtained afterfiltration and evaporation under reduced pressure (yield = 90 %). EPO 1H-NMR (300 MHz, CDCl3): ppm 0.00(s, 3H), 0.39-0.43(m, 2H), 1.50-1.62(m,2H), 2.6(s, IH), 3.31-3.47(m, 4H), 3.65(d, 2H)

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2006/101328, 2006, A1 Location in patent: Page/Page column 17-18

5
[ 111-45-5 ]
[ 1068-52-6 ]
[ 909570-34-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethylene glycol monoallyl ether With sodium In tetrahydrofuran for 3h; Reflux; Stage #2: sodium 2-bromoacetate In tetrahydrofuran at 20℃; Reflux;

Reference： [1]Location in patent: experimental part Barge, Alessandro; Cappelletti, Enrico; Cravotto, Giancarlo; Ferrigato, Aurelia; Lattuada, Luciano; Marinoni, Fabio; Tei, Lorenzo [Organic and Biomolecular Chemistry, 2009, vol. 7, # 18, p. 3810 - 3816]

6
[ 111-45-5 ]
[ 15075-50-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C / Reflux 1.2: 0.25 h / 0 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

Reference： [1]Current Patent Assignee: ECONOUS SYSTEMS - US2011/306771, 2011, A1

7
[ 111-45-5 ]
[ 103-16-2 ]
[ 1354967-78-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃;	8a (1 0g, 98 mmol), triphenylphosphine (30.8g, 1 17 mmol, 1 .2 eq), and 4-(benzyloxy)phenol (23.8g, 1 17 mmol, 1 .2 eq) were dissolved in DC (350 mL). DIAD (23.14 mL, 1 17 mmol, 1 .2 eq) in DCM (50 mL) was added dropwise to the reaction mixture and allowed to stir overnight. The mixture was concentratwed to a slurry before redissolving in Et20 (300 mL) and filtering any precipitated triphenylphosphine oxide. The filtrate was washed with aq. 2M NaOH (2 x 100 mL), water (100 mL) and brine (100 mL), before concentration to give an oily residue. This was further purified by FCC (eluent Et20/PE 10:90 for 2 column volumes, followed by 1 :4 to elute) to give 25.8g (93%) of 8b as a cream coloured solid.
71%	With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃;

Reference： [1]Current Patent Assignee: UNIVERSITY OF NOTTINGHAM - WO2012/4549, 2012, A1 Location in patent: Page/Page column 20-21
[2]Mistry, Shailesh N.; Baker, Jillian G.; Fischer, Peter M.; Hill, Stephen J.; Gardiner, Sheila M.; Kellam, Barrie [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3852 - 3865]

8
[ 22353-40-8 ]
[ 111-45-5 ]
2-(2-(allyloxy)ethoxy)-3-chloro-5-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%		To a solution of 2-allyloxyethanol (5.8 g, 57 mmol, 1.1 eq.) in dry THF (10 mL), was added NaH (1.37 g, 57 mmol, 1.1 eq.). After stirring at room temperature for 30 min, the solution was dropped into a solution of 2, 3-dichloro-5-nitropyridine (10 g, 52 mmol, 1 eq.) in THF (10 mL) at -20 C. The reaction was stirred for 1 hr. at room temperature, quenched with water (50 mL), and extracted with EtOAc. The organic phase was washed with water, dried over Na2S04, and concentrated to give compound 73 (13 g, 97%) as a brown oil.

Reference： [1]Patent: WO2016/103037,2016,A1 .Location in patent: Paragraph 00680

9
[ 111-45-5 ]
[ 31001-77-1 ]
3-methoxy-3-methyl-2,11-dioxa-7-thia-3-silatridecan-13-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 2,2-dimethoxy-2-phenylacetophenone for 0.666667h; UV-irradiation;

Reference： [1]Cao, Jinfeng; Zuo, Yujing; Wang, Dengxu; Zhang, Jie; Feng, Shengyu [New Journal of Chemistry, 2017, vol. 41, # 16, p. 8546 - 8553]

10
[ 111-45-5 ]
[ 55357-38-5 ]
2-allyloxyethyl phosphorylcholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		3.06 g (20 mmol) of phosphorus oxychloride and 40 mL of dichloromethane were placed in an eggplant flask (300 mL), and the mixture was stirred at 0 C. 20 mL of a mixed dichloromethane solution of 204 mg (2 mmol) of ethylene glycol monoallyl ether and 158 mg (2 mmol) of pyridine was slowly added dropwise, and the mixture was stirred at 0 C. for 1 hour and at room temperature for 1 hour. Excess of phosphorus oxychloride and dichloromethane were distilled off and dried under reduced pressure. To the obtained crude phosphoric acid chloride was added 40 mL of pyridine, and the mixture was stirred at 0 C. 2.76 g (10 mmol) of Corinthsirat was added while thoroughly stirring, and the mixture was stirred at room temperature for 24 hours. Water (20 mL) was added to the reaction solution, and the mixture was further stirred at room temperature for 6 hours. Pyridine and water were distilled off, and the objective substance was purified by performing silica gel column (methanol: chloroform = 100: 100 ? 0) twice.Colorless solidYield 65%

Reference： [1]Patent: JP5751578,2015,B2 .Location in patent: Paragraph 0020

11
[ 111-45-5 ]
[ 2370-88-9 ]
C₂₄H₅₆O₁₂Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-tert-butyl-4-methyl-phenol In ethanol; isopropyl alcohol at 75 - 85℃; for 3h;	3 [Example 3] In a 1 L flask, 306 g (3 mol) of allyl glycol,Dibutylhydroxytoluene 0.08 g,Platinum-divinyltetramethyldisiloxane complex0.9g of ethanol solution (platinum concentration 3%),Then, 150 g of isopropanol was charged, and the mixture was heated and stirred at 75° C. under a nitrogen atmosphere.Then 1,3,5,7-tetramethylcyclotetrasiloxane120 g (0.72 mol) was added dropwise over 1 hour.After completion of the dropping, the reaction was carried out at 85° C., followed by vacuum concentration at 5 mmHg at 80° C. for 2 hours.To the resulting solution, 250 g of toluene was added and well stirred, and then 400 g of a 10% sodium chloride aqueous solution was washed with water in four portions.The upper layer was evaporated under reduced pressure at 5 mmHg at 80° C. for 3 hours to obtain 295 g of a colorless transparent liquid.The liquid had a viscosity of 579 mm2/s, a refractive index of 1.4630 and a hydroxyl value of 163.From the results of GPC, 1H (NMR and IR,It was confirmed that this liquid was the compound (B3) represented by the following formula (23).

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - JP2020/66577, 2020, A Location in patent: Paragraph 0087-0088

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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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

[ CAS No. 111-45-5 ]

Quality Control of [ 111-45-5 ]

Related Doc. of [ 111-45-5 ]

Product Details of [ 111-45-5 ]

Safety of [ 111-45-5 ]

Application In Synthesis of [ 111-45-5 ]

[ 111-45-5 ] Synthesis Path-Upstream 1~10

[ 111-45-5 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 111-45-5 ]

Alkenyls

Aliphatic Chain Hydrocarbons

Ethers

Alcohols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 111-45-5 ]