CAS 35661-39-3 N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanine (HCID 6364642)

Names & identifiers

Preferred name: N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanine
IUPAC: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
English name: FMOC-Ala-OH
Molecular formula: C18H17NO4
Molecular weight: 311.33

Names & synonyms

35661-39-3N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-alanineDTXSID001245823N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanineEINECS 252-660-6NSC 334296FMOCAlaOH NovabiochemRefChem:823140DTXCID501676675252-660-6Fmoc-Ala-OHFmoc-L-alanine

Show more names

FMOC-ALAFMOC-L-ALAFomc-Ala-OHFmoc-ALFmoc-DL-Alanine

N-Fmoc-L-alanineFMOC-L-ALA-OHMFCD00037139L-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acidN-(9-Fluorenylmethoxycarbonyl)-L-alanineSCHEMBL119044Fmoc-L-Alanine monohydrate

Database identifiers

CAS: 35661-39-3
PubChem CID: 6364642
DTXSID: DTXSID001245823
ChEMBL: CHEMBL4284055
UNII: 352A2N82BU
EC Number: 252-660-6
Nikkaji: J256.555B

Properties

Computed structural properties

XLogP: 3.1
Topological polar surface area: 75.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 5
Heavy atoms: 23
Formal charge: 0
Complexity: 430

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives

Physical DescriptionWhite to light yellow solid; [EMD Millipore MSDS]

Physicochemical properties

Melting point: 147 · 147-153 °C (lit.)
alpha: -19 · -19 º (c=1,DMF)
Boiling point: 451.38 °C · 451.38°C (rough estimate)
Density: 1.2626 · 1.2626 (rough estimate)
refractive index: -18.5 ° · -18.5 ° (C=1, DMF)
storage temp.: 30 °C · Store below +30°C.
solubility: DMSO (Slightly), DMF (Sparingly), Methanol (Slightly)
form: Solid
pka: 3.91 · 3.91±0.10(Predicted)
color: White
optical activity: 20 · [α]20/D 18°, c = 1 in DMF
Water Solubility: Soluble in water.
BRN: 2225975 · 2225975
Major Application: peptide synthesis
InChI: 1S/C18H17NO4/c1-11(17(20)21)19-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,19,22)(H,20,21)/t11-/m0/s1
InChIKey: QWXZOFZKSQXPDC-NSHDSACASA-N
SMILES: C[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O
CAS DataBase Reference: 35661 · 35661-39-3(CAS DataBase Reference)
UNSPSC Code: 12352209 · 12352209
NACRES: 26 · NA.26
CAS Number Unlabeled: 35661 · 35661-39-3
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P271-P280
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 24 · 24/25-36/37/39-27-26
WGK Germany: 3 · 3
HazardClass: IRRITANT
HS Code: 29242990 · 29242990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 72.7% (8 of 11) of all reports.

Warning

H302 (18.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 11 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryNot considered hazardous by GHS classification; [EMD Millipore MSDS] See Fluorene.

Hazard Classes and CategoriesAcute Tox. 4 (18.2%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29242990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 24/25-36/37/39-27-26
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P271-P280

Chemistry & industry

Uses & manufacturing

UsesUsed in chemical and peptide syntheses; [EMD Millipore MSDS]

Applications · 2 items

DescriptionFMOC-Ala-OH is a versatile reagent used in Fmoc solid-phase peptide synthesis.

UsesFMOC-Ala-OH is potentially useful for proteomics studies and solid phase peptide synthesis techniques. Alanine is one of the simplest amino acids - a methyl group as the side chain. This small side chain confers a high degree of flexibility when incorporated into a polypeptide chain. The Fmoc group is typically removed with a base such as pyridine - an orthogonal de-protection strategy to the acid labilie Boc group.

Preparation methods · 1 item

PreparationA solution of the Fmoc-OX derivatives (20 mmol) in 100 mL acetone was added dropwise to a stirred solution of Alanine (20 mmol) and NaHCO3 (50 mmol) in 100 mL water. After stirring overnight the reaction mixture was concentrated under reduced pressure and then extracted with CH2Cl2 (50 mL) to remove the unreacted Fmoc-OX derivatives. The reaction mixture was cooled and acidified with 10% HCl to congo red litmus paper to give a white solid, which was filtered and washed with water several times, dried to give a white solid (FMOC-Ala-OH).Yield=89.5%.