Conditions | Yield |
---|---|
With Cumene hydroperoxide at 60 - 120℃; under 7500.75 Torr; Temperature; Pressure; | 99% |
With Cumene hydroperoxide at 60 - 120℃; under 7500.75 Torr; Temperature; Pressure; | 98% |
With 1-phenylethyl hydroperoxide In ethylbenzene at 30 - 50℃; under 750.075 Torr; Pressure; Temperature; Reagent/catalyst; | 98% |
Conditions | Yield |
---|---|
With resin IRA-440 In dichloromethane for 24h; Ambient temperature; | 98% |
With strong basic ion-exchange resin IRA 440 In dichloromethane for 24h; Product distribution; Ambient temperature; other basic ion-exchange resins; other glycerol dihalohydrins; other solvents and time; | 98% |
With calcium hydroxide inactive form; |
(C4H9)3SnOCH(CH2Cl)2
A
tributyltin chloride
B
chloroacetone
C
epichlorohydrin
Conditions | Yield |
---|---|
63% decompn. at 210°C (1 h); | A n/a B 5% C 95% |
γ,γ-dichloropropanol
epichlorohydrin
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; Temperature; | 94.1% |
3-chloroprop-1-ene
A
1-chloro-3-methoxypropan-2-ol
B
3-monochloro-1,2-propanediol
C
epichlorohydrin
Conditions | Yield |
---|---|
With dihydrogen peroxide; TS-1 In methanol; water; 1,2-dichloro-benzene at 25 - 40℃; for 1h; Product distribution / selectivity; | A n/a B n/a C 94% |
Conditions | Yield |
---|---|
With water; sodium hydroxide at 50℃; for 0.00833333h; Time; Temperature; Concentration; | 92.4% |
With potassium hydroxide |
Conditions | Yield |
---|---|
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 0 - 20℃; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With HT4-c823 In water at 149.84℃; under 750.075 Torr; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature; Flow reactor; chemoselective reaction; | A 18.9% B 80.5% |
(R,S)-2-hydroxy-3-chloropropyl p-toluenesulfonate
epichlorohydrin
Conditions | Yield |
---|---|
With sodium ethane-1,2-diolate In ethylene glycol at 20℃; for 0.25h; | 79% |
Conditions | Yield |
---|---|
With calcium hydroxide 1.) H2O, r.t., 1 h, 2.) hexane, 6 h; | 77% |
Conditions | Yield |
---|---|
Stage #1: glycerol With hydrogenchloride; Adipic acid In water at 120℃; for 8h; Stage #2: With calcium hydroxide | 67.5% |
With phosphorus trichloride | |
With hydrogenchloride anschl. mit Aetzkali; |
Conditions | Yield |
---|---|
With sodium ethane-1,2-diolate In ethylene glycol at 20℃; for 0.25h; | 58% |
With potassium hydroxide levorotatory form; |
2,3-Dichloro-1-propanol
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
D
epichlorohydrin
Conditions | Yield |
---|---|
With epoxide hydrolase from Agrobacterium radiobacter AD1; halohydrin dehalogenase from Agrobacterium radiobacter AD1; Tris-SO4 buffer In water at 30℃; for 20h; pH=7.5; kinetic resolution; Further byproducts given; | A n/a B n/a C 49.5% D n/a |
dihydrogen peroxide
3-chloroprop-1-ene
A
water
B
epichlorohydrin
Conditions | Yield |
---|---|
With titanium-containing zeolite In methanol at 35℃; Mechanism; Solvent; | A n/a B 29.8% |
Conditions | Yield |
---|---|
With molybdenum blue; dihydrogen peroxide; bis(tri-n-butyltin)oxide In chloroform at 25℃; for 10h; | A 1% B 48 % Turnov. |
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
beim Stehenlassen; |
Conditions | Yield |
---|---|
With catalysts |
epichlorohydrin
Conditions | Yield |
---|---|
With calcium hydroxide | |
With sodium hydroxide Herstellung eines mit Chlor-36 markierten Praeparats; |
1-bromo-3-chloro-propan-2-ol
A
hydrogen bromide
B
epichlorohydrin
Conditions | Yield |
---|---|
at 0℃; | |
at 0℃; Geschwindigkeit; | |
at 25℃; Geschwindigkeit; |
diethyl ether
1,3-Dichloro-2-propanol
water
A
allyl alcohol
B
epichlorohydrin
diethyl ether
1,3-Dichloro-2-propanol
A
propene
B
allyl alcohol
C
epichlorohydrin
ethanol
1,3-Dichloro-2-propanol
A
1,3-diethoxy-isopropanol
B
epichlorohydrin
Conditions | Yield |
---|---|
at 100℃; |
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 100% |
With zinc(II) chloride In water at 60℃; for 8h; regioselective reaction; | 96% |
In water at 0 - 5℃; for 4h; | 92% |
Conditions | Yield |
---|---|
With sodium carbonate; N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; | 100% |
With potassium carbonate In acetone for 20h; Heating; | |
With potassium carbonate In butanone Heating; | |
With potassium carbonate In acetone; toluene | 13.5 gm (61%) |
With sodium hydroxide |
Conditions | Yield |
---|---|
With iron(III) chloride at 20 - 70℃; for 24.1667h; | 100% |
With tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate for 0.666667h; Heating; | 99% |
With cerium(IV) triflate at 80℃; for 0.0833333h; | 93% |
Conditions | Yield |
---|---|
Stage #1: phenol With sodium hydroxide In water at 25℃; for 0.666667h; Stage #2: epichlorohydrin In water at 30 - 35℃; for 16h; | 100% |
With n-Bu4NOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h; | 91% |
With n-BuNOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h; other aryl alcohols, var. phase transfer catalysts, var. reaction time; | 91% |
Conditions | Yield |
---|---|
With hydrogen bromide at -60℃; for 16h; | 100% |
With dimethylbromosulphonium bromide In acetonitrile at 20℃; for 0.333333h; | 98% |
With ammonium cerium(IV) nitrate; tetrabutylammomium bromide In tert-butyl alcohol for 1.5h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane for 12h; Ambient temperature; | 100% |
With hydrogenchloride In water | 100% |
With chloro-trimethyl-silane; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 1h; ring opening reaction; | 99% |
epichlorohydrin
bis(3-chloro-2-hydroxypropyl)sulfide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogen sulfide monohydrate; sodium hydroxide In methanol; water at 6℃; | 100% |
With hydrogen sulfide; tetrabutylammomium bromide In toluene at 20 - 25℃; Solvent; Temperature; Reagent/catalyst; | 96% |
With hydrogen sulfide |
diisopropylamine
epichlorohydrin
1-Chlor-2-hydroxy-3-diisopropylamino-methyl-propan
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 100% |
In water |
Conditions | Yield |
---|---|
With lithium bromide at 20℃; for 5h; | 100% |
With Ni2+-metallodendrimer grafted on mesoporous polymethacrylate based Sepabeads EB-EP-400 In neat (no solvent) at 20℃; for 0.5h; Reagent/catalyst; Solvent; Green chemistry; regioselective reaction; | 97% |
With BiCl6(3-)*2C4H10N2*ClH*3H(1+)*H2O at 20℃; for 0.116667h; Neat (no solvent); regioselective reaction; | 96% |
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 100% |
In ethanol at 20℃; under 2585.81 Torr; for 0.0166667h; microwave irradiation; | 65% |
(2-hydroxyethyl)(methyl)amine
epichlorohydrin
1-Chlor-2-hydroxy-3-(N-methyl-N-2-hydroxyethyl)-amino-propan
Conditions | Yield |
---|---|
at 40 - 70℃; | 100% |
In water at 13 - 34℃; for 1.41667h; | |
In isopropyl alcohol |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h; | 100% |
Stage #1: 1H-indol-4-ol; epichlorohydrin With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h; Stage #2: With ammonium chloride In water | 99% |
With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h; | 99% |
4-phenyl-Δ2-1,2,4-triazoline-5-thione
epichlorohydrin
4-phenyl-3-(1-chloro-2-hydroxypropylthio)-1,2,4-triazole
Conditions | Yield |
---|---|
In ethanol at 20℃; for 5h; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide; Aliquat 336 In cyclohexane Heating; | 100% |
With sodium hydroxide; Aliquat 336 In cyclohexane Heating; | 99% |
With sodium hydroxide; Aliquat 336 In cyclohexane for 4h; Heating; | 99% |
trimethylsilyl cyanide
epichlorohydrin
4-chloro-3-trimethylsiloxybutyronitrile
Conditions | Yield |
---|---|
With erbium(III) triflate at 0 - 20℃; for 0.166667h; regioselective reaction; | 100% |
ytterbium cyanide In tetrahydrofuran at 25℃; for 0.3h; | 91% |
Conditions | Yield |
---|---|
With dmap; CrTTPCl at 60℃; under 37751.8 - 40337.5 Torr; for 18h; | 100% |
With triphenylphosphine; phenol at 120℃; under 30002.4 Torr; for 14h; | 100% |
With triethylamine; binaphthyldiamino Zn(II) salen-type compex In dichloromethane at 100℃; under 25858.1 Torr; | 100% |
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 100% |
isoselenocyanatotrimethylsilane
epichlorohydrin
3-Chloro-2-trimethylsiloxypropyl selenocyanate
Conditions | Yield |
---|---|
potassium selenocyanate In hexane at 40℃; for 24h; | 100% |
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 100% |
pyridinium perchlorate
epichlorohydrin
Conditions | Yield |
---|---|
With pyridine In ethanol for 3h; Product distribution; Heating; further cycloimmonium salts; | 100% |
With pyridine In ethanol for 3h; Heating; | 100% |
4-methylpyridinium perchlorate
epichlorohydrin
Conditions | Yield |
---|---|
With picoline for 1h; Heating; | 100% |
Conditions | Yield |
---|---|
With yttrium(III) chloride In dichloromethane for 36h; Ambient temperature; | 100% |
N-(1-chlorohexafluoro-1-methylethyl)benzenesulfinimidoyl chloride
epichlorohydrin
C12H10Cl3F6NOS
Conditions | Yield |
---|---|
In tetrachloromethane at 25℃; for 48h; | 100% |
N-(2-chlorohexafluoroisopropyl)-p-toluenesulfinimidoyl chloride
epichlorohydrin
C13H12Cl3F6NOS
Conditions | Yield |
---|---|
In tetrachloromethane at 25℃; for 48h; | 100% |
N-cyclohexyl-cyclohexanamine
epichlorohydrin
1-Chloro-3-dicyclohexylamino-propan-2-ol
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 100% |
(2-trimethylsilylprop-2-en-1-yl)tributylstannane
epichlorohydrin
Conditions | Yield |
---|---|
With ethylaluminum dichloride In dichloromethane at -78℃; for 19h; | 100% |
2-Allylphenol
epichlorohydrin
1-(2-allyl-phenoxy)-3-chloro-propan-2-ol
Conditions | Yield |
---|---|
With pyridine In chloroform; water; phenol | 100% |
With piperidine Heating; |
epichlorohydrin
p-cyclohexylphenol
2-[(4-cyclohexylphenoxy)methyl]oxirane
Conditions | Yield |
---|---|
With sodium hydroxide for 1h; Reflux; | 100% |
With sodium In isopropyl alcohol 1.) 10 min., reflux, 2.) 16 h., room temp.; |
epichlorohydrin
bis(2-bromo-2-chloropropyl)(2-bromo-3-chloropropyl)phosphonate
Conditions | Yield |
---|---|
With phosphorus tribromide at 0 - 40℃; | 100% |
Conditions | Yield |
---|---|
With chiral oligo-(salen)Co(OTs) complexes; lutidinium p-toluene sulfonate In acetonitrile at 4℃; for 4h; | 100% |
With (R,R)-(salen)Co(H2O); 3 A molecular sieve In various solvent(s) at -15℃; | 97% |
With C57H68N4O8(2-)*Co(3+)*C7H7O3S(1-); C56H66N2O6(2-)*Co(3+)*C7H7O3S(1-) In tetrachloromethane at 4 - 20℃; for 6h; stereoselective reaction; | 95% |
With Co(salen) macrocycles 1(OTs) In tert-butyl methyl ether at 20℃; for 9h; optical yield given as %ee; enantioselective reaction; | 91% |
With Co(salen) macrocycles 1(OTs) In tert-butyl methyl ether at 20℃; Kinetics; enantioselective reaction; |
Product Name: Epichlorohydrin (CAS NO.106-89-8)
Molecular Formula: C3H5ClO
Molecular Weight: 92.52g/mol
Mol File: 106-89-8.mol
EINECS: 203-439-8
Boiling point: 116.1 °C at 760 mmHg
Storage Temperature: Refrigerator (+4°C) + Flammables area
Flash Point: 33.9 °C
Density: 1.205 g/cm3
Refractive index: n20/D 1.438(lit.)
Stability: Stability Unstable. Flammable - note wide explosion limits and low flash point. Vapours may flow along surfaces to source of ignition. Contact with strong oxidisers may lead to fire. Incompatible with strong acids, strong bases, strong oxidizing agents, metal salts, amines, aluminium, chlorine and a variety of chlorine compounds, most com
Index of Refraction: 1.443
Molar Refractivity: 20.37 cm3
Molar Volume: 76.7 cm3
Surface Tension: 35.6 dyne/cm
Enthalpy of Vaporization: 33.98 kJ/mol
Vapour Pressure: 22 mmHg at 25°C
XLogP3-AA: 0.5
H-Bond Donor: 0
H-Bond Acceptor: 1
Structure Descriptors of Epichlorohydrin (CAS NO.106-89-8):
IUPAC Name: 2-(chloromethyl)oxirane
Canonical SMILES: C1C(O1)CCl
InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
InChIKey: BRLQWZUYTZBJKN-UHFFFAOYSA-N
Product Categories: Chlorepoxypropane (Epichlorohydrin); Organics; Oxiranes; Simple 3-Membered Ring Compounds
Epichlorohydrin (CAS NO.106-89-8) is a highly reactive compound,it is often used in the production of plastics,glycerol, and elastomers. Epichlorohydrin is a versatile precursor in the synthesis of many organic compounds. Epichlorohydrin is also used in water purification and paper reinforcement,such as in the food industry to manufacture coffee filters,tea bags, and sausage/salami casings.
Epichlorohydrin can be manufactured from allyl chloride in two steps:
1. | skn-rbt 10 mg/24H open | JIHTAB Journal of Industrial Hygiene and Toxicology. 30 (1948),63. | ||
2. | eye-rbt 100 mg/24H MOD | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,769. | ||
3. | dni-hmn:hla 2700 µmol/L | MUREAV Mutation Research. 92 (1982),427. | ||
4. | sce-hmn:lym 10 nmol/L | CARYAB Caryologia. 34 (1981),261. | ||
5. | spm-mus-ihl 5 mg/m3 | MUREAV Mutation Research. 85 (1981),287. | ||
6. | orl-mus TDLo:1200 mg/kg (female 6-15D post):TER | JTEHD6 Journal of Toxicology and Environmental Health. 9 (1982),87. | ||
7. | ihl-rat TCLo:50 ppm/6H (male 50D pre):REP | TXAPA9 Toxicology and Applied Pharmacology. 68 (1983),415. | ||
8. | orl-rat TDLo:60 g/kg/81W-I:CAR | GANNA2 Gann. Japanese Journal of Cancer Research. 71 (1980),922. | ||
9. | ihl-rat TCLo:100 ppm/6H/30D-C:CAR | JJIND8 JNCI, Journal of the National Cancer Institute. 65 (1980),751. | ||
10. | ipr-mus TDLo:2400 mg/kg/8W-I:NEO | TXAPA9 Toxicology and Applied Pharmacology. 82 (1986),19. |
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 202.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 11 , 1976,p. 131.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Community Right-To-Know List. EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.
Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion, skin contact, intravenous, and intraperitoneal routes. Moderately toxic by inhalation. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by inhalation: respiratory, nose, and eyes. Human mutation data reported. A skin and eye irritant. A sensitizer. Flammable liquid when exposed to heat or flame. Explosive reaction with aniline. Reaction with trichloroethylene forms the explosive dichloroacetylene. Ignition on contact with potassium tert-butoxide. Violent reaction with sulfuric acid or isopropylamine. Exothermic polymerization on contact with strong acids, caustic alkalies, aluminum, aluminum chloride, iron(III) chloride, or zinc. When heated to decomposition it emits toxic fumes of Cl−.
Hazard Codes : T
Risk Statements :45-10-23/24/25-34-43
R45:May cause cancer.
R10:Flammable.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R43:May cause sensitization by skin contact.
Safety Statements :53-45
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2023 6.1/PG 2
WGK Germany: 3
OSHA PEL: TWA 2 ppm (skin)
ACGIH TLV: TWA 0.5 ppm (skin); Animal Carcinogen
DFG MAK: DFG TRK: Animal Carcinogen, Suspected Human Carcinogen
NIOSH REL: Minimize exposure
DOT Classification: 6.1; Label: Poison
For occupational chemical analysis use NIOSH: Epichlorohydrin, 1010.
Epichlorohydrin , its CAS NO. is 106-89-8, the synonyms are 1-Chloro-2,3-epoxy propane ; 2-(Chloromethyl)oxirane ; 3-Chloro-1,2-epoxypropane .
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