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2-Amino-2-phenylacetic acid

2-Amino-2-phenylacetic acid structure

CAS No:
2835-06-5
Formula:
C8H9NO2
Chemical Name:
2-Amino-2-phenylacetic acid
Synonyms:
RARECHEM AK ML 0501;(.+/-.)-alpha-Phenylglycine;(+/-)-benzeneaceticaci;.alpha.-amino-,(+-)-Benzeneaceticacid;-Aminobenzeneaceticacid;Benzeneacetic acid, alpha-amino-, (±;Benzeneaceticacid,-amino-,(+-)-;PHENYLGLYCINE(D,L-)
Categories:
Biochemical Engineering > Amino Acids and Derivatives

Description

white amorphous powder

Solid

Alpha-phenylglycine is an amino acid with a structure in which a phenyl ring is bonded to the alpha-carbon of glycine. It has a role as a human metabolite.

2-Amino-2-phenylacetic acid is a natural compound that has been identified as a selective inhibitor of cyclooxygenase 2 (COX-2), and it exhibits antiinflammatory activity. It has been shown to inhibit COX-2 at low concentrations and to be less potent than aspirin in inhibiting COX-1. It is also an amide, with a molecular weight of 296. In order to determine the structure of it, XRD data was collected from the monosodium salt form of the compound. The ester hydrochloride form was used for enzyme activity assays because it is more soluble in water than the free base form. The synthesis of 2-Amino-2-phenylacetic acid was achieved through a two step process involving amide formation and hydrolysis.

2-Amino-2-phenylacetic acid Basic Attributes

Molecular Weight：

151.17

Exact Mass：

151.16

BRN：

3197862

EC Number：

220-608-1

NSC Number：

206293|32070|24619|7928

TSCA：

TSCA listed

Color/Form：

White to off-white

HScode：

29224999

Characteristics

PSA：

63.32000

XLogP3：

-1.7

Appearance：

White to off-white Crystalline Powder

Density：

1.2023 (rough estimate)

Melting Point：

290 °C (subl.)(lit.)

Boiling Point：

273.17°C (rough estimate)

Flash Point：

128.4±24.0 °C

Refractive Index：

1.5810 (estimate)

Water Solubility：

115g/L(100 ºC)

Storage Conditions：

Store below +30°C.

Vapor Pressure：

8.86E-06mmHg at 25°C

PKA：

1.94±0.10(Predicted)

Critical Temperature & Pressure：

Keep in dark place,Inert atmosphere,Room temperature

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

F,C

safety instructions：

24/25-45-36/37/39-26-16

Marks：

F,C

Precautionary statement(s)：

S24/25

Hazard Statements：

11-34

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH Entry Terms：

2-phenylglycine

2-Amino-2-phenylacetic acid Use and Manufacturing

Methods of Manufacturing

Benzaldehyde is obtained by cyclization, hydrolysis, and neutralization. Put the ammonium bicarbonate and sodium cyanide solution into the reaction pot, add benzaldehyde dropwise under stirring, and react at 75-80°C for 3 hours to obtain phenylhydantoin. Pump into the autoclave, add sodium hydroxide solution, raise the temperature, vent the ammonia gas generated by the reaction for 1 hour, and then hydrolyze it at 130-160°C for 3 hours. Discharging, adding HCl to neutralize to pH=6-7, centrifuging and drying to obtain DL-2-phenylglycine. There is also a glyoxylic acid route, which can reduce production costs and solve the problem of high toxicity of traditional process raw materials.

Uses

Used to manufacture L-phenylglycine

DL-α-Phenylglycine is used as a reagent in the synthesis of benzoquinone-amino acid conjugates which have antibacterial activity.

Manufacturing Info：

Benzeneacetic acid, .alpha.-amino-: ACTIVE|Benzeneacetic acid, .alpha.-amino-, (.alpha.S)-: ACTIVE|Benzeneacetic acid, .alpha.-amino-, (.alpha.R)-: ACTIVE

Computed Properties

Molecular Weight:151.16
XLogP3:-1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:141
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

188591-75-5

53934-78-4

Suppliers(3)

2835-06-5

Suppliers(15)

Downstream Products

Glycine

Ammonia

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Guide of 2-Amino-2-phenylacetic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Synthesis Route
Downstream Products
Recommended Suppliers
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2-Amino-2-phenylacetic acid

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