CAS 701-99-5 Phenoxyacetyl chloride (HCID 69703)

Names & identifiers

Preferred name: Phenoxyacetyl chloride
IUPAC: 2-phenoxyacetyl chloride
English name: Phenoxyacetyl chloride
Molecular formula: C8H7ClO2
Molecular weight: 170.59

Names & synonyms

Phenoxyacetyl chloride701-99-52-phenoxyacetyl chloridePhenyloxyacetyl chlorideAcetyl chloride, 2-phenoxy-NSC 9808EINECS 211-862-4RefChem:861526211-862-4InChI=1/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6HAcetyl chloride, phenoxy-Phenoxyacetylchloride

Show more names

SKL1266AKOS BBS-00003927Acyl chloride kindPhenoxyacetyl chloriphenoxy-acetylchloridLABOTEST-BB LT00643586Acetylchloride,phenoxy-PhenoxyacetylChloride>

MFCD00000726NSC-9808phenoxyacetic acid chloridePhenoxyacetic acid chloride; Phenoxyacetyl chloride; Phenoxyethanoyl chloride; Phenyloxyacetyl chloridephenoxylacetylchloride2-phenoxyacetylchloridephenoxy acetyl chloridephenoxy-acetyl chloride

Database identifiers

CAS: 701-99-5
PubChem CID: 69703
DTXSID: DTXSID1061029
UNII: NS65CKB849
EC Number: 211-862-4
Nikkaji: J62.847F

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 11
Formal charge: 0
Complexity: 130

Physicochemical properties

Melting point: 100 · 100-100.5 °C
Boiling point: 225 · 225-226 °C (lit.)
Density: 1.235 g/mL · 1.235 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.534(lit.)
Flash point: 227 °F · 227 °F
storage temp.: Store at RT.
form: Liquid
color: Clear slightly yellow to brown
Water Solubility: Reacts with water.
Sensitive: Moisture Sensitive
BRN: 607585 · 607585
InChI: InChI=1S/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2
InChIKey: PKUPAJQAJXVUEK-UHFFFAOYSA-N
SMILES: C(Cl)(COC1=CC=CC=C1)=O
CAS DataBase Reference: 701 · 701-99-5(CAS DataBase Reference)
FDA UNII: 65 CKB849 · NS65CKB849
NIST Chemistry Reference: Acetyl chloride, phenoxy-(701-99-5)
EPA Substance Registry System: Acetyl chloride, phenoxy- (701-99-5)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05,GHS07
Signal word: Danger
Hazard statements: 314 · H314-H335
Precautionary statements: 261 · P261-P271-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338
target organs: Respiratory system
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: C
Risk Statements: 14 · 14-34-36/37
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 3265 · UN 3265 8/PG 2
WGK Germany: 3 · 3
F: 10 · 10-19
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: II
HS Code: 29189090 · 29189090
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 BSTOT · Skin Corr. 1BSTOT SE 3
Limited Quantities: 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Peroxide Forming Chemical · 3 items

Phenoxyacetyl chloride

D: Other compounds that may form peroxides

Kelly

Hazard Classes and CategoriesSkin Corr. 1B (100%)

Safety data

F: 10-19
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 2
hs_code: 29189090
risk_code: 14-34-36/37
Signal word: Danger
Symbol(GHS): GHS05,GHS07
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: II
target organs: Respiratory system
Hazard statements: H314-H335
Limited Quantities: 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications: Skin Corr. 1BSTOT SE 3
Precautionary statements: P261-P271-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationAcetyl chloride, 2-phenoxy-: ACTIVE

Applications · 2 items

UsesAcylation of D- and DL-WV with phenoxyacetyl chloride, followed by cleavage of the t-butyl ester,afforded the penultimate penicilloic acids. Phenoxyacetyl chloride was used in the synthesis of series of macrocyclic bis-β-lactams, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester, N-protected guanosine derivatives, useful in RNA synthesis, phenyloxyketene, for cycloaddition to imines leading to β-lactams. Treatment of iminophosphoranes with phenoxyacetyl chloride afforded respectively the trans- and cis-3-(acylamino)-p-lactams. By the oxidative addition of stannous fluoride to allyliodide, with 1, 2-O-isopropylidene-D-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallylester, which is in turn converted into 2-deoxy-D-ribose. The 4-disubstituted P-lactams (4a-c and 6a-b) were prepared through the reaction of N,N-diphenylhydrazones and N-methyl-N-phenylhydrazones of ketones with phenoxyacetyl chloride/Et3N in dichloromethane.

UsesPhenoxyacetyl chloride was used in the synthesis of:series of macrocyclic bis-β-lactams5-phenyl-6-epiphenoxymethylpenicillin benzyl esterN-protected guanosine derivatives, useful in RNA synthesisphenyloxyketene, for cycloaddition to imines leading to β-lactams